Does anyone dream about retiring internationally?

We have briefly discussed it.

One of the big things keeping us here in the US is the complexity of filing US tax returns when living in a different country. From a “figure out the tax returns” point of view it is just easier to stay in the US, file only US taxes, and make use of the US health care system, rather than moving to Canada (which would be easy since I have dual citizenship). That plus inertia are the two biggest things that keep us in the US. Inertia is big also. We like where we live.

Sadly I think that taxing US citizens anywhere in the world encourages us old people to stay here and use US health care, while encouraging young very smart students who are already studying abroad to consider renouncing US citizenship. It think that it is the very smart young folks that the US would want to keep.

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Well, if you split your time you can live in both places and be taxed in the US. Some countries also have tax agreements. It varies a lot based on a number of factors.
I don’t see many young people renouncing US citizenship anytime soon. It’s often easier for most people to acquire the second citizenship and keep the first. And if you aren’t making any money in the US, there are usually tax agreements so you end up filing out a simple form. I lived abroad in many countries ( and in Canada) for about a decade and I never felt as though it was egregious. In some years, I made decent money also.
One bonus to being a US citizen is being able to live anywhere and still collect SS. That isn’t common in most countries.
I think if you wanted to live in Canada, you likely could make it work pretty easily.

Well, I’d like to own property in several countries and go back and forth at will. A pied a terre in London (and why not Paris, too,) a small home in Italy.

But also a home base of some sort in Maine. It’s possible I’d satisfy the international urges by extablishing a long term relationship with some sort of bnb arangement. (That I could stay for a month or two or three, without making some fixed commitment.)

With the covid concerns, not going anywhere And, not making decisions based on my kids. I love them, but this “dream” would include the ability to get back and forth easily.

I do wish my kids would move, however. Get out of the rut of living in the same place (more or less,) all their lives. Of course, I hope it would be someplace I like, I’d visit them frequently.

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We will likely stay in the US, and probably on the east coast, because that’s where most of our family is. However, we have talked about buying a place on Grand Cayman or less likely, Turks and Caicos. (NOTE - we have never checked into the actual cost of doing so and both islands our probably beyond our means).

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I’m not sure there is a logistically easy way to relocate and get cheaper healthcare if you don’t have dual citizenship. But I imagine a lot of the savings would be eaten up by trips back to US.

I think healthcare cost are often much less in other parts of the world than the US. Some folks who retire abroad plan major operations and an annual trip home for access to US care. Naturally, these things cannot always be planned.
Healthcare’s certainly a large part of the total picture. Even in the US, many stay close to major medical centers if they have a major condition.

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Our plan is to relocate somewhere here in the US that is less expensive and use the savings from that to stay long term (1-3 months) each year in various countries that we like.

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This has always been on my list. I would like to spend the winter someplace warm. I was thinking about Mexico or Panama. But, ShawWife is Canadian and prefers the cold and is seriously dyslexic, so doesn’t pick up languages well at all. That killed Mexico or Panama.
For a while, we were compromising on living for the winter on a houseboat in Sausalito – a compromise because it is neither warm not cold. I loved the view (and one of our kids and now both are in the Bay Area).

We have also thought about retiring to Canada. In fact, my Plan B if my business was not performing well was to move to Canada, which ShawWife would be happy with. We have a lovely house in the Laurentians, which we completely renovated last year. It is good for summers (though she would love to be there in the winters also).

Now our plans are confounded by buying a new house in the same town where we raised our kids to replace the house in which we raised them. The new house is grandfathered on the banks of a river and surrounded by land that is permanently conservation land or agricultural land. So, it feels like being in a nature preserve, or as one visitor said, “I feel like I just walked into Adirondack State Park.” We’re doing some spiffy renovations with a fancy architect so this place is going to be nicer than the Laurentians place. So now I just need someplace warm where they speak English. Sadly, I’m guessing that is Florida rather than California or Belize. Easier to get to. Better for taxes.