@Charles *******
If you’re actually going to stay 20+ years and can learn some Thai, def consider going the work permit/visa route and applying for citizenship.
It’s not as bad as it used to be with 5+ year processing times.
But you will have to have lived and “worked” and filed tax returns for 3 years and will have to learn to speak Thai, possibly read and write it or have a Thai wife to get enough points to qualify.
The savings on buying a condo in the thai quota without a thai company or buying a house and actually owning it can alone be worth it, not to mention not having to deal with immigration again, being able to much more easily do business and work if that’s something you might want to do.
A lot will change in 20 years so don’t think in terms of just what your situation is now.
And learning to speak Thai when you’re going to be here for 20+ years can only help.
Also, it’s cheaper, excluding the value of your time to learn thai and meet the other needed requirements.
Something to consider.