Taxation and Teaching in Italy
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Taxation and Teaching in Italy
My understanding of tax law is that US citizens working abroad are expected to pay income taxes to the US, and that a treaty between Italy and the US ensures US citizens abroad aren't having to pay income taxes to Italy, too. But I keep reading on ISR how salary for year 3 IT's in Italy plummets due to the collection of Italian taxes, which doesn't happen in the first two. Can someone shed some more light on this? Especially as it relates to Americans? Are these stories from non-US citizens and therefore not applicable?
Response
There isnt much more to expound on, you summarized it well enough. Your first year in Italy you pay very little tax (you pay some), your second year you pay a little more, bit still manageable. Your third year you are paying full taxes. Unless your at an upper tier IS where youre banking serious coin, or the IS is subsidizing you with a tax benefit (or housing), most ITs cant afford to stay past their second year, or they stay the third and sign a document they will handle their taxes themselves at the end of the year and then they leave the tax authorities holding an empty bag.
The treaty is not indefinite and applies to Americans, its fixed to a limited amount of time. You can offset your US taxes with one of three foreign deductions/exemptions/credits against your Italian taxes, but that third year your paying full taxes to Italia. Youre using your share of resources and program benefits, you have to pay your share of the costs since at three years the Italian government assumes youre no longer visiting.
The treaty is not indefinite and applies to Americans, its fixed to a limited amount of time. You can offset your US taxes with one of three foreign deductions/exemptions/credits against your Italian taxes, but that third year your paying full taxes to Italia. Youre using your share of resources and program benefits, you have to pay your share of the costs since at three years the Italian government assumes youre no longer visiting.
Re: Taxation and Teaching in Italy
No, the stories are true and are from US citizens.
US citizens working abroad are required to file every year with the IRS and report their foreign-earned income regardless of which country they are in. If that income is over $103,900 (in 2018), they must pay US taxes on it. Any taxes paid to the other country can be credited, which can bring down the amount you are taxed, IF you make over $103,900. You wouldn’t even come close to that working in Italy. If you make more, you could pay taxes to both countries. (Note: You will have to pay US taxes on any income you have in the US, such as interest, capital gains, or summer job income, regardless.)
The treaty you are referring to is not about avoiding paying taxes to both countries. The treaty is about teaching tax free for two years in Italy. (More countries are included in the treaty, by the way. Other nationalities are also included, not just Americans. and it goes both ways - foreign teachers from the countries on the list can teach in the US for two years tax free as well.) After the two years are up you start to pay full income taxes in Italy because you live there, just like non-teaching foreigners have been doing since they arrived. You can still file a credit with the IRS, so you would not be double taxed. It’s a nice tax benefit teachers (and some researchers) have for two years that others don’t.
The issue with Italy is that the salaries are so low it’s hard to make ends meet once the Italian taxes kick in, even though you’re not being double taxed. It’s a shame, but it’s reality.
US citizens working abroad are required to file every year with the IRS and report their foreign-earned income regardless of which country they are in. If that income is over $103,900 (in 2018), they must pay US taxes on it. Any taxes paid to the other country can be credited, which can bring down the amount you are taxed, IF you make over $103,900. You wouldn’t even come close to that working in Italy. If you make more, you could pay taxes to both countries. (Note: You will have to pay US taxes on any income you have in the US, such as interest, capital gains, or summer job income, regardless.)
The treaty you are referring to is not about avoiding paying taxes to both countries. The treaty is about teaching tax free for two years in Italy. (More countries are included in the treaty, by the way. Other nationalities are also included, not just Americans. and it goes both ways - foreign teachers from the countries on the list can teach in the US for two years tax free as well.) After the two years are up you start to pay full income taxes in Italy because you live there, just like non-teaching foreigners have been doing since they arrived. You can still file a credit with the IRS, so you would not be double taxed. It’s a nice tax benefit teachers (and some researchers) have for two years that others don’t.
The issue with Italy is that the salaries are so low it’s hard to make ends meet once the Italian taxes kick in, even though you’re not being double taxed. It’s a shame, but it’s reality.
Discussion
Concur with @alexout, Italy doesnt really compensate in coin, but lifestyle. Happens every year, the new arrivals are so excited, and then it doesnt go away, and only rarely do new arrivals tire of the Italia lifestyle, especially in one of the major metro cities. They try all the usual strategies, trying to get a spouse credentialed or employed so that they can benefit from two incomes, and trying to move up into one of the elite tier ISs, but as to years flies by and the end of the second year approaches the tears come and they leave, some of them try to economize but most of the activities that make Italy so enjoyable require coin.
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Re: Taxation and Teaching in Italy
Love Italy but just left for this reason. Be prepared to have someone to support you, or a second income, and absolutely no expectation to save.
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Re: Taxation and Teaching in Italy
chiliverde wrote:
> Love Italy but just left for this reason. Be prepared to have someone to
> support you, or a second income, and absolutely no expectation to save.
In the interest of full disclosure, I'll have a generous pension from a public system if/when I attempt to teach in Europe. La dolce vita sure seems attractive, as my wife and I loved our two weeks there 7 years ago. It strikes me as potentially frustrating to see whatever side income I have from a "2nd act teaching career" FALL if I taught for a 3rd year, but I could likely absorb the hit.
> Love Italy but just left for this reason. Be prepared to have someone to
> support you, or a second income, and absolutely no expectation to save.
In the interest of full disclosure, I'll have a generous pension from a public system if/when I attempt to teach in Europe. La dolce vita sure seems attractive, as my wife and I loved our two weeks there 7 years ago. It strikes me as potentially frustrating to see whatever side income I have from a "2nd act teaching career" FALL if I taught for a 3rd year, but I could likely absorb the hit.
Reply
@ILMathTeachr
Your US pension is taxable under Italian law if you reside in Italy for 183 or more days in a year after your two years. Italia considers you an Italian "resident" under two tests: a life centered in Italy, or being registered in the population registry as living more than 183 days a year in Italy, you would thus be subject to taxation of world wide income, even a US pension, though you will not be double taxed on it, you will not have to pay US taxes if you pay Italian taxes, and if you do pay US Taxes, then you will be able to credit the US tax payed towards your Italian taxes.
Regardless, the tax rate for you is going to be about a third of your gross income. Kids make a huge difference, mainly in the form of tuition places/waivers, Italia considers them compensation just as coin is and with an average value of €10K/yr/each, they are taxed at the normal rate so about 30% of €10K is €3K, and with the average salary in Italia around €2500/mth it will take you about one and a half months of net salary just to pay the taxes on a childs tuition waiver (because you owe taxes on that €2500/mth salary which after taxes is €1750) have two kids at your IS and thats three months salary before you pay any expenses like living.
Two other important factors, 1) Italy now isnt like it was 7 years ago. 2) Your experience as a tourist for two weeks is nothing like living there.
Working in Italy is like working anywhere, you spend most of your day and week working, because you have a job, called teaching. Your highlight of the week might be eating out at a cafe with a bottle of table wine and people watching, maybe seeing the sun set, and then a midnight walk past the fountain. That will be it for the entire week, and it will get old really fast, just as the pan sauce and pasta you make the rest of the week that you wash down with a glass of cheap wine (its too expensive to have more than a glass a day), will get old fast. Meanwhile your living like a Uni student, and youre saving absolutely nothing. All those awesome things like weekend trips to Venice, or down to the coast, or shopping in the boutiques or in Milan, you cant really afford to do. If you can scrape up the coin to do that or live a little better you wont have the time because you will be like most other Italians who have temporary contracts (meaning second and third jobs) you will be exhausted and will have no time.
Your US pension is taxable under Italian law if you reside in Italy for 183 or more days in a year after your two years. Italia considers you an Italian "resident" under two tests: a life centered in Italy, or being registered in the population registry as living more than 183 days a year in Italy, you would thus be subject to taxation of world wide income, even a US pension, though you will not be double taxed on it, you will not have to pay US taxes if you pay Italian taxes, and if you do pay US Taxes, then you will be able to credit the US tax payed towards your Italian taxes.
Regardless, the tax rate for you is going to be about a third of your gross income. Kids make a huge difference, mainly in the form of tuition places/waivers, Italia considers them compensation just as coin is and with an average value of €10K/yr/each, they are taxed at the normal rate so about 30% of €10K is €3K, and with the average salary in Italia around €2500/mth it will take you about one and a half months of net salary just to pay the taxes on a childs tuition waiver (because you owe taxes on that €2500/mth salary which after taxes is €1750) have two kids at your IS and thats three months salary before you pay any expenses like living.
Two other important factors, 1) Italy now isnt like it was 7 years ago. 2) Your experience as a tourist for two weeks is nothing like living there.
Working in Italy is like working anywhere, you spend most of your day and week working, because you have a job, called teaching. Your highlight of the week might be eating out at a cafe with a bottle of table wine and people watching, maybe seeing the sun set, and then a midnight walk past the fountain. That will be it for the entire week, and it will get old really fast, just as the pan sauce and pasta you make the rest of the week that you wash down with a glass of cheap wine (its too expensive to have more than a glass a day), will get old fast. Meanwhile your living like a Uni student, and youre saving absolutely nothing. All those awesome things like weekend trips to Venice, or down to the coast, or shopping in the boutiques or in Milan, you cant really afford to do. If you can scrape up the coin to do that or live a little better you wont have the time because you will be like most other Italians who have temporary contracts (meaning second and third jobs) you will be exhausted and will have no time.
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Re: Reply
PsyGuy wrote:
> @ILMathTeachr
>
> Your US pension is taxable under Italian law if you reside in Italy for 183
> or more days in a year after your two years. Italia considers you an
> Italian "resident" under two tests: a life centered in Italy,
> or being registered in the population registry as living more than 183 days
> a year in Italy, you would thus be subject to taxation of world wide
> income, even a US pension, though you will not be double taxed on it, you
> will not have to pay US taxes if you pay Italian taxes, and if you do pay
> US Taxes, then you will be able to credit the US tax payed towards your
> Italian taxes.
>
> Regardless, the tax rate for you is going to be about a third of your gross
> income. Kids make a huge difference, mainly in the form of tuition
> places/waivers, Italia considers them compensation just as coin is and with
> an average value of €10K/yr/each, they are taxed at the normal rate so
> about 30% of €10K is €3K, and with the average salary in Italia around
> €2500/mth it will take you about one and a half months of net salary just
> to pay the taxes on a childs tuition waiver (because you owe taxes on that
> €2500/mth salary which after taxes is €1750) have two kids at your IS and
> thats three months salary before you pay any expenses like living.
>
> Two other important factors, 1) Italy now isnt like it was 7 years ago. 2)
> Your experience as a tourist for two weeks is nothing like living there.
> Working in Italy is like working anywhere, you spend most of your day and
> week working, because you have a job, called teaching. Your highlight of
> the week might be eating out at a cafe with a bottle of table wine and
> people watching, maybe seeing the sun set, and then a midnight walk past
> the fountain. That will be it for the entire week, and it will get old
> really fast, just as the pan sauce and pasta you make the rest of the week
> that you wash down with a glass of cheap wine (its too expensive to have
> more than a glass a day), will get old fast. Meanwhile your living like a
> Uni student, and youre saving absolutely nothing. All those awesome things
> like weekend trips to Venice, or down to the coast, or shopping in the
> boutiques or in Milan, you cant really afford to do. If you can scrape up
> the coin to do that or live a little better you wont have the time because
> you will be like most other Italians who have temporary contracts (meaning
> second and third jobs) you will be exhausted and will have no time.
Thanks, PsyGuy. So, even if I had no trailing dependents, other than a spouse who has an EU passport, do you feel the pay for an IT in Italia is probably only sufficient for buying some cheap groceries, renting a decent flat, and dining out periodically?
If that's the case, wouldn't an extra USD 100K/year make things far more comfortable and enjoyable?
> @ILMathTeachr
>
> Your US pension is taxable under Italian law if you reside in Italy for 183
> or more days in a year after your two years. Italia considers you an
> Italian "resident" under two tests: a life centered in Italy,
> or being registered in the population registry as living more than 183 days
> a year in Italy, you would thus be subject to taxation of world wide
> income, even a US pension, though you will not be double taxed on it, you
> will not have to pay US taxes if you pay Italian taxes, and if you do pay
> US Taxes, then you will be able to credit the US tax payed towards your
> Italian taxes.
>
> Regardless, the tax rate for you is going to be about a third of your gross
> income. Kids make a huge difference, mainly in the form of tuition
> places/waivers, Italia considers them compensation just as coin is and with
> an average value of €10K/yr/each, they are taxed at the normal rate so
> about 30% of €10K is €3K, and with the average salary in Italia around
> €2500/mth it will take you about one and a half months of net salary just
> to pay the taxes on a childs tuition waiver (because you owe taxes on that
> €2500/mth salary which after taxes is €1750) have two kids at your IS and
> thats three months salary before you pay any expenses like living.
>
> Two other important factors, 1) Italy now isnt like it was 7 years ago. 2)
> Your experience as a tourist for two weeks is nothing like living there.
> Working in Italy is like working anywhere, you spend most of your day and
> week working, because you have a job, called teaching. Your highlight of
> the week might be eating out at a cafe with a bottle of table wine and
> people watching, maybe seeing the sun set, and then a midnight walk past
> the fountain. That will be it for the entire week, and it will get old
> really fast, just as the pan sauce and pasta you make the rest of the week
> that you wash down with a glass of cheap wine (its too expensive to have
> more than a glass a day), will get old fast. Meanwhile your living like a
> Uni student, and youre saving absolutely nothing. All those awesome things
> like weekend trips to Venice, or down to the coast, or shopping in the
> boutiques or in Milan, you cant really afford to do. If you can scrape up
> the coin to do that or live a little better you wont have the time because
> you will be like most other Italians who have temporary contracts (meaning
> second and third jobs) you will be exhausted and will have no time.
Thanks, PsyGuy. So, even if I had no trailing dependents, other than a spouse who has an EU passport, do you feel the pay for an IT in Italia is probably only sufficient for buying some cheap groceries, renting a decent flat, and dining out periodically?
If that's the case, wouldn't an extra USD 100K/year make things far more comfortable and enjoyable?
Reply
@ILMathTeachr
Yes, the range of salaries in the 1SD are about €2100/mth--€2800/mth, your tax rate is about 30% percent, the average of €2500/mth leaves you about €1800/mth. Looking at somewhere worth living like Rome (highest concentration of ISs), a comfortable western style flat/apartment will run you €1000/mth inside the city CBD and about €700/mth outside the CBD, thats half your net coin. Utilities will cost you about €150 including internet (no satellite). Groceries will cost you about €500/mth for two with just the basics, more with vino, and higher end food. A metro pass will cost you €35/each and your mobile with data about €70/each. Lets add that up:
€700 Housing (somewhere in the middle)
€150 Utilities
€500 Groceries (I assume you want to eat moderately well)
€140 Mobile
€70 Transportation
Thats using the minimums and basic costs and your at €1560 leaving about €190/mth for both of you as discretionary coin on an average salary after taxes. That's €6/day for the both of you, or about €3/each thats little more than an espresso and a bottle of water as luxuries on a daily basis.
If you have USD$100K/yr extra on the side your not an IT, your retired with a hobby thats teaching, why bother to do the teaching thing. Leadership will despise you, you wont put up with crazy directives and requirements, because you dont need the job, unlike everyone else who has to put up with it or leave the country your spouse is an EU citizen, and you dont need the coin, you can just leave and go home.
Yes, the range of salaries in the 1SD are about €2100/mth--€2800/mth, your tax rate is about 30% percent, the average of €2500/mth leaves you about €1800/mth. Looking at somewhere worth living like Rome (highest concentration of ISs), a comfortable western style flat/apartment will run you €1000/mth inside the city CBD and about €700/mth outside the CBD, thats half your net coin. Utilities will cost you about €150 including internet (no satellite). Groceries will cost you about €500/mth for two with just the basics, more with vino, and higher end food. A metro pass will cost you €35/each and your mobile with data about €70/each. Lets add that up:
€700 Housing (somewhere in the middle)
€150 Utilities
€500 Groceries (I assume you want to eat moderately well)
€140 Mobile
€70 Transportation
Thats using the minimums and basic costs and your at €1560 leaving about €190/mth for both of you as discretionary coin on an average salary after taxes. That's €6/day for the both of you, or about €3/each thats little more than an espresso and a bottle of water as luxuries on a daily basis.
If you have USD$100K/yr extra on the side your not an IT, your retired with a hobby thats teaching, why bother to do the teaching thing. Leadership will despise you, you wont put up with crazy directives and requirements, because you dont need the job, unlike everyone else who has to put up with it or leave the country your spouse is an EU citizen, and you dont need the coin, you can just leave and go home.
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Re: Reply
PsyGuy wrote:
> If you have USD$100K/yr extra on the side your not an IT, your retired with
> a hobby thats teaching, why bother to do the teaching thing.
Two words; HEALTH INSURANCE
If I sit at home in the US as a retiree, but under the age of 65, health insurance is over $21K annually to cover myself and spouse.
> If you have USD$100K/yr extra on the side your not an IT, your retired with
> a hobby thats teaching, why bother to do the teaching thing.
Two words; HEALTH INSURANCE
If I sit at home in the US as a retiree, but under the age of 65, health insurance is over $21K annually to cover myself and spouse.
Reply
@ILMathTeachr
two more words --Red Herring--, thats what your teaching angle is. You dont have to teach in Italy, your spouse is an EU citizen, you can get an EU passport, and even if you cant you can still reside with your spouse on a permanent resident basis in the EU, in Italy. You can sit on a sofa in Rome and do nothing and your health care on the public scheme will cost about €250/yr.
two more words --Red Herring--, thats what your teaching angle is. You dont have to teach in Italy, your spouse is an EU citizen, you can get an EU passport, and even if you cant you can still reside with your spouse on a permanent resident basis in the EU, in Italy. You can sit on a sofa in Rome and do nothing and your health care on the public scheme will cost about €250/yr.
Re: Taxation and Teaching in Italy
ILMathTeachr, with 100k coming in, you can do it. But I'd recommend first visiting again and staying for a month or two to try it out. Living in Italy is not at all like visiting it. Outside of tourism activities, almost nothing works smoothly. Decent housing is difficult to find. Workmen never come when they say they will. In Rome, at least, most apartments available to rent for 700-1,000 euros are old, shoddy, small, and furnished with grandma's discarded stuff. If you want something picturesque in a nice neighborhood, be prepared to spend 1,800+ euros a month, and that's if you're lucky enough to find something. As a foreigner, you might even get a special deal - higher rent. Driving is crazy, and public transportation is in crisis. (The trains are ok.) Taxi drivers are likely to rip you off. If you didn't get pickpocketed when you visited, a longer stay will most likely make it happen. You'll need to learn Italian, as English is not widely spoken outside of tourism areas. Depending on where you are in the country, the city may be filthy, with trash piled high in the streets. With a lot of money, you can avoid some of these issues, and put on blinders when you visit the countless sights. But living there can be frustrating and wears you down after a while. Be forewarned. Personally, there are other places in southern Europe I'd much rather live with a 100k income to keep me comfortable, or even way less (I've done it), and stick to visiting Italy on long weekends. Enjoy it and then escape. Oh, and then there's the issue of schools. I once asked a very experienced teacher who had taught all over Italy where the good schools were, because I was having a hard time finding one. Her answer? There aren't any. Go to Switzerland, she said.
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Re: Reply
PsyGuy wrote:
> @ILMathTeachr
>
> two more words --Red Herring--, thats what your teaching angle is. You dont
> have to teach in Italy, your spouse is an EU citizen, you can get an EU
> passport, and even if you cant you can still reside with your spouse on a
> permanent resident basis in the EU, in Italy. You can sit on a sofa in Rome
> and do nothing and your health care on the public scheme will cost about
> €250/yr.
@PsyGuy
I don't think I can just claim an Irish passport. When I looked up the rules, I have to actually have lived there for a not insignificant amount of time according to what I read. Nevertheless, my wife's Irish passport definitely makes it easy for us to go anywhere in the EU. Maybe we're idealizing Italy a bit; but my wife definitely wants to return to Europe for an open-ended stay, and I feel it'd be a great adventure to see how much 35 years of teaching math in the US translates to teaching in an IS. Could we afford to live off my pension and our combined savings? Probably. But I feel confident I won't want to spend the rest of my days sitting on my sofa.
@alexout
Maybe Spain would be a better fit with my ability to speak the language? I don't feel I'm 100% fluent, but speak it well enough to deal with the police in Ixtapa. I did learn enough Italian before our visit that I could competently ask directions on the street. I've never studied French, but my wife is passably fluent, but she has no interest in settling anywhere near Paris.
With that in mind, I'm interested to hear your other recs for places to try to settle. She has made a point that we'd benefit from finding someplace with easy access to rail transit.
> @ILMathTeachr
>
> two more words --Red Herring--, thats what your teaching angle is. You dont
> have to teach in Italy, your spouse is an EU citizen, you can get an EU
> passport, and even if you cant you can still reside with your spouse on a
> permanent resident basis in the EU, in Italy. You can sit on a sofa in Rome
> and do nothing and your health care on the public scheme will cost about
> €250/yr.
@PsyGuy
I don't think I can just claim an Irish passport. When I looked up the rules, I have to actually have lived there for a not insignificant amount of time according to what I read. Nevertheless, my wife's Irish passport definitely makes it easy for us to go anywhere in the EU. Maybe we're idealizing Italy a bit; but my wife definitely wants to return to Europe for an open-ended stay, and I feel it'd be a great adventure to see how much 35 years of teaching math in the US translates to teaching in an IS. Could we afford to live off my pension and our combined savings? Probably. But I feel confident I won't want to spend the rest of my days sitting on my sofa.
@alexout
Maybe Spain would be a better fit with my ability to speak the language? I don't feel I'm 100% fluent, but speak it well enough to deal with the police in Ixtapa. I did learn enough Italian before our visit that I could competently ask directions on the street. I've never studied French, but my wife is passably fluent, but she has no interest in settling anywhere near Paris.
With that in mind, I'm interested to hear your other recs for places to try to settle. She has made a point that we'd benefit from finding someplace with easy access to rail transit.
Reply
@ILMathTeachr
You could absolutely afford to do it on USD$100K/yr, and live well.
I would say if you want modern, picturesque and a western affluent neighborhood youre looking at €2000+/mth and thats not counting the fees for private services. Finding workmen that come on time is almost impossible, but its not something that happens too often, considering the wait time to schedule them in the first place is so long as to be impractical. The other issue is that most rental contracts you could get would essentially require you to make all repairs anyway. The only legal requirement a property owner must comply with is keeping the property habitable, but that require an inspection by an inspector of inhabitable and than you have to go to the housing office and file a complain and then they have a process and it would take you a year if not more to do it.
Driving in Italian cities is nuts, even if you have a scooter/Vespa. When i was there the big thing of thieves was to drive up to your scooter wherever you parked it and just load it into a truck and drive off with it. The metro is okay, but its not like anything in JP or SG or HK. There is a us vs. them mentality of locals towards tourists, their ethics for tourists is lower than it is for locals, lots of people will innocently and not so innocently try to rip you off. You dont have to learn Italian, as if you live in Rome with the coin you have you can afford to live in and around expat enclaves, where English is a norm.
There is a lot of filth, but part of the high cost of living in affluent neighborhoods is having private refuse collection that everyone participates in that reduces your exposure, but you are paying coin for it (and you still have to pay the municipal services).
I dont agree with @alexout about "good" ISs in Italy, there are tier 1 and elite ISs in Italy, but tier is regionally dependent and its disingenuous to compare Italy to Switzerland, lots of regions in the WE (France, Spain, etc.) fail in comparison to Switzerland.
I dont know if you can claim an Irish passport either, but I would talk to an expert in immigration law and explore options available to you (one option may be applying for an English passport and citizenship, that doesnt require residency and then using that to apply for an Irish passport in the future).
Italy is worth of idealization, its not a poo hole, and there are a lot pluses, but its not all unicorns, and rainbows and pixie dust and you dont see the depths of the uglier side as a tourist.
If Italy is what your goal is and its long time, i would look to living outside the CBD even the country and buying as opposed to renting. You will get more value for your euro.
I can respect your desire to challenge IE with your 35 years of US maths teaching experience, but to make it a fair challenge your going to want to learn the local language (Italian) if you want a valid measure. Though you need not sit on your couch you need not teach either, perhaps the EU and/or Italia will expose you to entirely different challenges and adventures but needing to teach or work in IE is a a red herring, you can do a lot with a 6 figure/yr retirement and edu need not be a part of it.
LCSA Spanish and Castilian Spanish are not the same Im sure you know. They are about as similar and different as the Queens English and American Standard English.
Well the highest concentration of ISs is in/near Paris but there are plenty of DSs with Academies that your EU passports would allow you to work in outside of Paris. Though finding those positions are largely advertised locally, and really arent difficult to find.
The vast majority of metro locations have highly accessible metro systems, its when you get out of those cities you have more of a reliance on buses than trains. So if you want trains major cities is where you want.
You could absolutely afford to do it on USD$100K/yr, and live well.
I would say if you want modern, picturesque and a western affluent neighborhood youre looking at €2000+/mth and thats not counting the fees for private services. Finding workmen that come on time is almost impossible, but its not something that happens too often, considering the wait time to schedule them in the first place is so long as to be impractical. The other issue is that most rental contracts you could get would essentially require you to make all repairs anyway. The only legal requirement a property owner must comply with is keeping the property habitable, but that require an inspection by an inspector of inhabitable and than you have to go to the housing office and file a complain and then they have a process and it would take you a year if not more to do it.
Driving in Italian cities is nuts, even if you have a scooter/Vespa. When i was there the big thing of thieves was to drive up to your scooter wherever you parked it and just load it into a truck and drive off with it. The metro is okay, but its not like anything in JP or SG or HK. There is a us vs. them mentality of locals towards tourists, their ethics for tourists is lower than it is for locals, lots of people will innocently and not so innocently try to rip you off. You dont have to learn Italian, as if you live in Rome with the coin you have you can afford to live in and around expat enclaves, where English is a norm.
There is a lot of filth, but part of the high cost of living in affluent neighborhoods is having private refuse collection that everyone participates in that reduces your exposure, but you are paying coin for it (and you still have to pay the municipal services).
I dont agree with @alexout about "good" ISs in Italy, there are tier 1 and elite ISs in Italy, but tier is regionally dependent and its disingenuous to compare Italy to Switzerland, lots of regions in the WE (France, Spain, etc.) fail in comparison to Switzerland.
I dont know if you can claim an Irish passport either, but I would talk to an expert in immigration law and explore options available to you (one option may be applying for an English passport and citizenship, that doesnt require residency and then using that to apply for an Irish passport in the future).
Italy is worth of idealization, its not a poo hole, and there are a lot pluses, but its not all unicorns, and rainbows and pixie dust and you dont see the depths of the uglier side as a tourist.
If Italy is what your goal is and its long time, i would look to living outside the CBD even the country and buying as opposed to renting. You will get more value for your euro.
I can respect your desire to challenge IE with your 35 years of US maths teaching experience, but to make it a fair challenge your going to want to learn the local language (Italian) if you want a valid measure. Though you need not sit on your couch you need not teach either, perhaps the EU and/or Italia will expose you to entirely different challenges and adventures but needing to teach or work in IE is a a red herring, you can do a lot with a 6 figure/yr retirement and edu need not be a part of it.
LCSA Spanish and Castilian Spanish are not the same Im sure you know. They are about as similar and different as the Queens English and American Standard English.
Well the highest concentration of ISs is in/near Paris but there are plenty of DSs with Academies that your EU passports would allow you to work in outside of Paris. Though finding those positions are largely advertised locally, and really arent difficult to find.
The vast majority of metro locations have highly accessible metro systems, its when you get out of those cities you have more of a reliance on buses than trains. So if you want trains major cities is where you want.