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Eastern Europe is expensive for the most part, even more expensive than the US in quite a few places.
Do not know much about South America, I do know that money goes a lot further judging by the amount of American expats that are retired living down there.
I'd agree that Thailand would give you the most for your money, won't leave you feeling isolated, and wide variety of things to see and do for fun and adventure. You'll find English available in most of the larger cities catering to tourists.
Weatherwise, Nov - Feb is probably best, unless you really like the heat and humidity. Lots of mosquitos at night, so I'd suggest using a good repellant with DEET.
Bangkok and surrounding areas have a good number of must-see spots. Chiang Mai (in the North) also has lots of expats and is an excellent city to base yourself in to explore the surrounding areas of that region of the country.
I agree that the food is cheap and tastes great!
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