I don’t wish I paid more although I did once write an article I still agree with in my town paper suggesting that we will all be better off if our town taxed us more and put it largely into schools. I mostly don’t begrudge the taxes I pay but I wish they were used a lot better. But, at one point, I added up how much I was paying in Federal tax, state tax, taxes for all of my employees, etc. and realized I have paid in taxes more than I ever thought I would make. I would love to see it go directly to support families in need.
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Pretty much sounds as though you are having similar thoughts as you did previously. However, I am not getting sucked into the same defensive mode I did the last time you discussed buying a home in Florida. I’m sure you will make the best decision for you, your family, and the many other relevant aspects of your personal and financial needs.
I will only add that I promise you will find MANY people from the Commonwealth of Massachusetts during the season. MANY.
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Well said. I pay quite a lot in taxes and my continued disappointment usually stems from how both state and federal government’s spend that money, but it’s more the federal expenditures that bother me.
I’d also add a couple general comments regarding “paying one’s fair share” (whatever that actually means):
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We’re talking about state income taxes. Every state needs revenue and therefore all people pay taxes in one form or another: income, sales, property and so forth.
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Criticisms about gaming the system or dodging one’s “obligation” to pay their fair share of taxes doesn’t carry much weight when between 57% and 40% of US households (depending on the year) don’t pay a cent in federal income taxes and a portion of those people also receive free money back from the IRS.
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No, I don’t think it would.
Withdrawals from IRAs, 401(k)s, and other tax-deferred retirement funds in the US are not recognized under Puerto Rico Act 22. Thus, moving to the island won’t reduce the distribution tax. The same applies to Social Security benefits and other pension payments.
Sabalier Law - How Are Retirement Plans Taxed in Puerto Rico? | Sabalier Law
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And elsewhere too.
GEHA does offer rebates with Medicare. We’re on the High Option now. While H doesn’t plan to retire for another five years and we’ll still be on his plan til then, I want to get ducks in a row and thoroughly understand our options. I’ll be eligible for Medicare in Jan. 2026, and I need to make sure I’m well-covered six ways by Sunday.
Thanks to everyone who has given me feedback! I’ve gotten some great leads to pursue.
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I think generally it is not wise to let the tax tail wag the income dog.
Unless those saved taxes will make a material difference in your life, taxes should be way down the list of reasons to live or not live in a particular place, IMO.
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Agree. Tax effects are but one factor.
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Wow 
. What an insult to Floridians everywhere.
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Agree. Especially since the native Floridians are bright, AND the west coast of FL is filled with people from the northeast…especially in the winter.
Very insulting comment to anyone who lives in Florida.
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Agree. I wonder how my town would rank. But then again, I love listening to everyone’s life story. Even the Walmart cashier has an interesting life to me.
(That’s a big reason why I’m on here. I love reading about everyone’s perspectives and stories)
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Boston may have a concentration of certain groups of population - as is the case with large cities. Although Boston has a concentration of academic institutions, some of these have certainly gone away from ‘truth’ and have some haywire ideas (goes against CC guidelines to expound any further).
Difficult to make generalizations about regions, cities, etc. in the US when it comes to the population ‘on average’ - most of us interact and are drawn to “our own people” - whatever that is and may not deal with a lot of people in the ‘general public’. Some areas have friendly neighborhoods - and just down the street from ‘friendly neighbors’ have a whole different feel (our next door neighbor had that experience, when they built a home about 9 houses down the street) - they eventually got to know the one next door neighbor, but on our end we had summer BBQ parties and a lot more of neighbors looking out for neighbors.
When one lives far from all the MDs, medical services, the gym or other recreational, as well as grocery and all the other things - shopping, eating out, sporting events, fine arts events, one would really miss the conveniences and things in a more populated area.
After a ‘busy MD week’, we actually had no appointments this week. So nice in retirement to have the free time.
Thanks.
If looking for intellectual depth and interest, then I’d highly recommend retiring around Stanford. Around here, I’m actually the one without intellectual depth and interest. 
I think my answer was incomplete, as it didn’t address your point about moving an existing 401k account to PR.
This article suggests you can’t roll a US based account to a PR account.
Rollovers Between Puerto Rico and U.S. Retirement Savings Plans — Ascensus
My comment was not intended as an insult and was focused on where we are on the west coast of Florida (so folks from Miami or Orlando or even Tampa were not included). Moreover, what is interesting is inherently in the eye of the beholder. But, in the Boston area, the folks I know and see at dinner parties include folks working on the cure to specific cancers or ebola, presidents of universities, folks thinking about climate finance, ending the war in Ukraine, how to construct an off-ramp in the Middle East to create a path toward a durable peace, the intricacies of international trade and the causes of economic inequality. I’ve been at parties with a Supreme Court Justice and a Senator. My book group has three Harvard professors from different fields, an environmentalist, a tech lawyer with a PhD in literature, etc.
These folks might not be nearly as interesting to @patsmom or @ClassicMom98 as they are to me. I love learning what people at the cutting edge are doing. People tried to introduce ShawWife to me back in the dark ages. They described me to her (where and what I had studied and my first job, which were pretty prestigious by CC standards) and she said, “He sounds boring to me.”
Where we are in Florida, many the folks are from the Midwest and Northeast – @thumper1, it seems more Midwest, but both. Most of the people are retired, though I recently met a couple of real estate developers (one from the MW and one who does super-luxury houses in the NE). ShawWife organized a party on my mother-in-law’s street and we met neighbors including a software engineer and a CPA who are from the NE, a psychiatrist from the MW who is winding down his practice and a teacher (also from the MW, I think). There was also a cybersecurity software sales guy, a retired couple who are not doing well, and a former NFL player and his wife who were not able to make it. The average age of the community seems pretty high. When we lower the average age, we are talking pretty old.
Pretty much all of these people are nice and I’m not intending to be critical when I say that they are less interesting to me than a friend who is discovering ways to do some surgeries on kids without drugs by blocking pain without drugs, someone involved in nuclear fusion startups or someone thinking about how one brings the population of a country like Colombia together after the end of a long civil war.
It could also be that the community we would love exists but because we are not full time residents and/or didn’t build our communities there, we don’t know it. So far, we have not come across a community comparable to Boston. I’m sure if we were there six months a year, we’d probably meet a broader swath of people than we do in a six week stay.
@SOSConcern, I don’t disagree that some of the folks at academic institutions have gotten a bit lost. While I don’t believe we should be discriminating against blacks or other groups nor set up environments in which people feel unwanted or uncomfortable, I believe the implementation of DEI at some of these institutions has gone awry and has diverged from a desirable original conception in a variety of undesirable ways. Interestingly, quite a number of the professors I know would probably agree that the institutions have lost their way in that regard.
@sushiritto, I tried. I really like the Stanford area (especially the buzzy excitement of interesting startups), but the South Bay didn’t speak to her (actually because of lack of moisture). ShawSon was in the Stanford area, then San Francisco and ShawD moved in with him for four years. We rented a houseboat in Sausalito for three months at a time in the winters (I know not the best weather but better than New England) and sublet a studio space in an artist building nearby. I even co-founded a tech company with a Stanford engineering/MBA grad so I had a bunch of excuses to go out there. We met lots of interesting people there – a bit tech-focused but working on very interesting problems. She found a pretty good arts community. But, I could not persuade her to move – it would be harder to afford a home in expensive communities on both coasts. But, failure to persuade her has reduced my state taxes.
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@simon3, thanks again. This makes sense. I understand why they would want to entice people to move firms that exports services to the island. This would add taxes and likely jobs and skills to the island. I don’t see why it would help PR to reduce the taxes on withdrawals from retirement accounts. So no rollovers of US based accounts makes sense.
Yeah, it’s probably best you stay in Boston.
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I had to smile when I read “dinner parties”. Yes, we do host them and attend them now and then. But they tend to be with the folks we already know… mostly based on couples with coworkers from hubby (and I know them too from working same place years ago). We usually go or beer/dinner with various combos of those couples on Friday night…. kind of an opt-in event hubby coordinates via group texts. It’s fun that other people meet new people at dinner parties, like I’ve seen in the movies. Shows that we really are in a bit of a rut. But ha, it’s a comfortable rut. Tis probably a good thing that we want to stay put. We might not have the right mindset to settle somewhere new.
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