>  I don't know if I could take such a huge step when I retire.


for people without extensive overseas experience it would probably be a bad idea outside of the financial benefits.  Cultural differences are fun when you are young but once you are old and grumpy if you are not already familiar with them they will likely just drive you nuts!   

The money requirement on the part of Thailand is justified by the thinking that if you don't have $20,000 locked away, you don't really have enough money to live there long-term.   The only crappy thing I have heard about this deposit is that a few people have changed their minds about retiring there and had some difficulty getting the money back.  They always DO get it back but the fact that there is a bunch of red tape involved with the process indicates that theft might be a possibility.