I haven't done so, but have done a fair bit of investigation. The most technically correct answer I can give is that it depends on where you're going and how yo

I haven't done so, but have done a fair bit of investigation. The most technically correct answer I can give is that it depends on where you're going and how you leave things in the US. First, where you're going. You obviously want to go somewhere with better healthcare than the U.S., which isn't all that difficult to find. The ? becomes what your obligations will be as a somewhat permanent resident and how you can maintain that status legally. That's really going to be location dependent, but you should look and look hard before you leap, because the consequences could be unpleasant if you screw up. I believe there are agencies that cater to potential expats like yourself, and if you're really serious about this you should talk to one of them to make sure you don't step on any landmines in the process. As for the second ?, The US assumes that you continue to owe US taxes as long as you maintain your citizenship, and they make it difficult to give that up. I don't know exact figures, but you are exempt up to something like $78000 of income and are allowed to write any foreign taxes you pay on that off, but as long as you are a US citizen you're on the hook. If you move to Singapore and strike it rich, unless you pay the IRS you could have extradition hearings in your future. I'm pretty sure the deficient US health care system would be pretty low on your list of worries in that case. Again, this is the sort of thing a professional could tell you more about, but this is definitely out there. I don't want to advocate giving up your citizenship lightly, but know that the US is unique in this sort of taxation and making a fortune abroad without paying US taxes would almost certainly be viewed as some sort of tax evasion if you didn't proceed very carefully.