Wherever you live you will have challenges/problems. That is the way it is.
Having been in LOS, I know a little cf to the newcomer ie fools paradise.
My personal experience is that being >50yo is a big advantage re visa.
No $$$ - better not even think of living here.
Why?
Employment restrictions - teaching English pays poorly in the Nth.
A business - in your Thai partner's name generally=potential problems.
Good luck to the risk takers.