In case you're unaware, there's also r/IWantOut on Reddit, which is all about this kind of stuff.
I'm 'out' (currently Lisbon, previously both Rio long-term and short-term in Medellin) but since I've always tried to get away from native English speakers, in order to have a more 'authentic' experience, I can't say what's good for Americans. Key to me has been language. Get at least intermediate in the one that's spoken where you're going.
If you can be location-independent, it's quite worthwhile to go spend a month or three in some of your top picks but beware, a short stay can seem like a long vacation (meaning the expat 'honeymoon phase' might make you like some place more than you would if you actually had to live there).
I've had a couple of wonderful experiences vacationing in the Algarve. What's it like to actually live in Portugal?
I'm a Canadian, with a combined admiration and disdain for U.S. society. Actually, that was redundant :). Also, I have dual-Canadian German citizenship and am running a largely telework-friendly business.
I've spent a few 5 month winters down in the Algarve, mostly to escape the cold in SW France while still being able to grab some waves (surfer).
Weather's generally sunny, landscape (as you, the OP know) is surreal, and the people, both locals and expats, are generally friendly.
A bit insular compared to Lisbon area, not a whole lot going on (expect for summer when it's apparently a complete holiday zoo).
The language is next to impossible to grok (can get by well enough in Brazilian Portuguese but the dialect down here is just something else, they seem to swallow their words). Fortunately the Portuguese as a people generally speak decent English.
Dirt cheap in the off-season (was renting a massive modern apartment with 20 foot ceilings for 500 euros per month) and internet is decent for being out in the sticks, had @8mbs/2mbs near Sagres.
Can definitely reccomend the Algarve, just not sure about long-term, it's truly another world ;-)
I have yet to make it down to the Algarve but people I know have gone and loved it (though some have said it's largely British, even when getting something from the local market where the owner-counter person is a Brit).
Living in Portugal is great, in my opinion. Being low-cost really helps, too. Lisbon is one of the prettiest/lovliest cities I've ever lived in (though it took me over 6 months to start to see it). And the short day-trips are well worth it (Arrábida+Cabo Espichel, Sintra, Cascais, etc). Renting a 1-bdrm in the city center is US$500/mo so it's hard to complain. Porto is awesome, too, and cheaper than Lisbon.
I'm 'out' (currently Lisbon, previously both Rio long-term and short-term in Medellin) but since I've always tried to get away from native English speakers, in order to have a more 'authentic' experience, I can't say what's good for Americans. Key to me has been language. Get at least intermediate in the one that's spoken where you're going.
If you can be location-independent, it's quite worthwhile to go spend a month or three in some of your top picks but beware, a short stay can seem like a long vacation (meaning the expat 'honeymoon phase' might make you like some place more than you would if you actually had to live there).