lol Okay I totally over looked your Veteran status and am realizing it right now, my mistake.
$10k< what I meant was that you probably don't want to try to enter the country w/ $10k.
My numbers are probably a little high, I like to play it safe when estimating. Maybe they'll help someone wondering
Yep, furnished rentals.
For freelancing destinations if I had to puck another country to spend MN winters in it would be Chile because they really seem to be pushing the whole startup culture and that startupchile website is totally worth looking at.
Otherwise I'd think Europe would be awesome because they have so many conferences to network. But I guess what's throwing me off is what your looking for in a new location, because taxes and cost of living are. I mean I'm sure the cost of living and tax situation on paper in Somalia would be appealing. Ok, that's an extreme, but would Russia be extreme?
To me it seems like if you're working remote you have a unique opportunity to go where you want to go...
But oh! Just came to mind.
If cost of living is a thing you want to know about this website is really neat: http://www.numbeo.com/cost-of-living/
Sorry for all the nonsense, but I think you'll enjoy the link because it's super useful (and interesting) if you haven't been using it to check around.
Best a luck!