I daughter-was 8 years old, got a stamp for overstay for two days- no fine. I was not aware of situation as she is a dual citizen but entered Thailand with an Australian passport. I did not know the law at time.
Don't sell your home in the USA, go to live in Thailand for a year before making an important decision. I would recommend you to rent the place and not even buy a condo.
Thailand is a very good place to explore then if you like it you can stay for a longer time.
Thai language (driver?) licence if a new one will last for two years. You have to renew before it expires. For the bank you keep a few 1000THB and keep your phone SIM card( number you provided to the bank)- convert it to a prepaid sim and put a few hundred THB in to keep your number going. If you change your phone number/Sim, next time you come back it is a little paper work for changing a phone number.
I got bored after a year in Thailand too. I am now back in Australia. A long holiday is very boring for me Lol.
It is not that hard to get a motorbike licence in Thailand. A paper/ online exam is in English, the training is by watching a traffic rule vdo then a practical exam takes only less than 10 minutes. The fee is about $10 to $20.
You should come by a tourist visa first then explore Thailand and SE Asian countries before making a decision. If you travel to North Eastern Thailand, please contact me -I have a place for you to stay. Good luck with your adventures!