Somewhere that does not seem to get a mention on this thread is India and SE Asia, I have been able to spend two of the last four winters in these places and India in particular is still quite affordable, prices are rising but you can still live on £10/$16 a day. A room in a guesthouse or hotel can be had for £5/$8 per night and deals can be negotiated for longer periods, if you eat where the locals do there is no need to cook but a taste for spicy food does help.
English is widely spoken and there is plenty of interesting company from both locals and other foreigners who will mostly be Brits, Germans and other Europeans. Public transport is cheap and goes everywhere but driving/riding is a bit of an adventure not for the faint hearted, local motorcycles are small and inexpensive, you won't need that 1000cc superbike with 50 mph rarely being reached.
It is also becoming popular for health tourism with modern medical and dental clinics often having UK trained doctors and dentist at a fraction of the cost of the US, some people seem to combine getting away from the winter with getting something sorted out that is not covered by their health service at home.
There are few if any money making possibilities but if you have a small income or want to make a lump sum go further it is somewhere worth considering.
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