I'll try to answer the original question.
I should note that my responses are mostly Asian, since I'm fluent in Chinese (makes things much easier). Still, none of these countries are too alien.
You have a couple things to consider here. Most people leaving the US would want a place that speaks English; that's do-able, thanks to the economic strength of America, and a couple centuries of British imperialism. Most Americans would like a capitalist country.. socialism pretty much infects the world, so it's gonna be hard to match this. Consequently be ready to get taxed out your shitter. If you don't have an actual income, though, and are living on savings, this isn't usually a great problem; just prep yourself for the VATs.
Most of the world is also what we would consider leftist. Bite your toungue and don't lash out; it makes you unpopular. With that in mind, there are a couple places I think an average American could live in with relative ease.
Canada is always an OK choice. I'm sure you already know the main points, but I'll try to gloss over. It's a modern country in the areas people live in. You can get guns with a good bit of paperwork as I understand it, and the standard of living is comparable. It does get cold. It is a socialist-esque country (like the rest of the world), so you kinda have to bite your toungue as an American import.
Presuming you have some quantity of money already saved up, the Philippines are not a bad choice; many speak English, your money is pretty powerful, and the climate's good. Infrastructure in most places is modern. Gun ownership for citizens is easy, but it's controlled around cities. Still, all the gun bans extend only to places outside one's own home, so you still have the option of defense in your abode. Lots of expats in the Philippines, so you'd be in good company.
Singapore is a good option, but there's a good bit of learning to do, and you'd definitely be an outsider; but to an extent everybody is. There are expat clubs and such, though, so you wouldn't be alone. It's a lot different, but I know a bunch of people living in S'pore that're Americans and get by rather well. It's quite different, but a very nice place to live.
Australia is also good and modern, speaks English, and your money goes pretty far. I don't know anything about their gun laws except that the far majority of semi autos are banned.
South Africa in some ways is good, but oh my freaking gad crime is bad. My aunt has barbed wire in her backyard and a gun in every room of her house/apartment. She's been highjacked in her car twice (she drives a Benz, so YMMV), and she has security bars on her windows. Still, many speak English, the climate's nice, and from what I hear, it's pretty much a gunowner's paradise.
None of these choices are as good as staying in America. At least for now, anyway. I'd like to stay and fight, but if things get unrecoverable, I'm packing my bags and heading off. Freedom-snatchers from the left and right are just waiting to pounce and make america a world-class shithole, and I'm just going to hope I can help enough to keep them away. Fight hard.