FYI, unless you're willing to live like a bum Thailand isn't a cheap place to live. My rent is 75% of what I paid for a Nob Hill apartment and my car payment is

FYI, unless you're willing to live like a bum Thailand isn't a cheap place to live. My rent is 75% of what I paid for a Nob Hill apartment and my car payment is 100% more expensive (import duties). If you're willing to live like a bum you've got tons of options, including moving out to Nowhere USA. My parents spend part of their year in Tucson, AZ. I've seen ok homes for sale there for under 100k. The used car market is incredible as is the case in most of the US. You'd have to deal with chain restaurants and strip malls but at the fraction of the cost of most urban centers. I would recommend setting up your company offshore. It's not as complicated as people make it out to be (unless they're selling their services) and I know plenty of long-term expats who have done so without issue. Chances are if you're asking this question here you're not going to be on anyone's radar with your company. The US does want you to: 1) File taxes regardless of residence. If you're declaring personal income you're exempt up to 95k or so but even if you make under that you're expected to file. Having said that I don't know anyone who does or anyone who has ever had an issue. I talked to the IRS once about it (I was young and wasn't making over the limit and hadn't filed taxes for years) and they suggested to get up to speed to just file back reports and ask for the exemption as normal. 2) I guess now you're supposed to declare any foreign bank account with more than 10k in it. I've never heard of this being enforced in any way. As far as I know probably your easiest route it to move to HK. They seem to have the most lax immigration policies and it's easy to set up a company there. Rent is like central SF (same size/price ratio). If you're not selling products in HK you're not liable for taxes (standard tax haven stuff). Or just setup your company there and live somewhere else. If you do that though you're going to have to deal with immigration somehow because you'll permanently be a tourist. If you're a tourist in most of these destinations you're looking at moving in and out of the country 3 - 4 times a year or more. Between my first and second company I was living here and fell into a sort of immigration limbo, having to live as a tourist for quite a while. I assure you that going in and out of the country to keep your paperwork current gets old really fast. This was assuming you're a US citizen. If not ignore the US-specific info.