My advise would be to buy one property in your legal residence, so that would be the Canary Islands based on you being an EU pp holder.
Then I would simply rent the other nine months of the year wherever you want and as 'winter' is the high season in the Canaries you shouldn't have too much problem renting your own place out, in fact you could make a packet over xmas/new years.
Sounds cool, try not to take too much on-board from the resident doom-mongers of TT.
Not sure that it is still true, but there are countries where if you have a certain level of income, you can get residence.
Rainy season in Thailand isn't terrible. It's not like the UK where it rains all the time. It is hot and rainy and then it clears. It storms and then it clears. I spent 2.5 years in Thailand including 3 rainy seasons and there are actually some positives about the rainy season in that it can be cooler and the temperatures more comfortable. My point is you really don't know what you might be missing.
Try a country for a few weeks or a few months and see if it's the one before you invest in buying places. In the end, you might find your home in the country of your passport.
Ruth
One mistake newbie expats make; They buy a place b4 living there a year or more. B4 they really know how things really work, regardless of laws and retrictions. Or work ethic of repairmen.
The longer you live in a location, as you learn... you find out you don't like it so much.
Or you learned about a cooler (in many ways,) a pueblo or twenty minutes away. In Quepos, Costa Rica, a guy told me he lived just out of town. It was always 15 digrees cooler there than in town.
And an extranjero selling a house, can get screwed bad.
If buyers find out when you have to leave, they will lowball you at the "last minute" for your sacrifice.
