I think I like your second idea Robert. I know I want to stay abroad for at least a year, and I do need to see if teaching English in Thailand is something that really fits me. And I know if I don't work my money will too quickly run out as I have no retirement benefits coming in.
So if you knew you wanted to stay in Thailand for a year, at least, and you are considering possibly teaching English there, then is it best to just get a tourist visa for 60 days instead of the "retirement" visa for one year?