Just re-read your post. Just a bit concerned at your situation, re. Aus financial planning for retirement, Thai financial planning medical insurances etc and what do you intended to do exactly in Thailand.
Drinking in bars all day is good fun but it won't really do every day all day for retirement. I really feel you have quieten a difficult situation that requires a good deal of planning from people much more knowledgeable than me.
I would have loved to have retired there but couldn't make it work !!!