My job is remote. I decided to relocate from big European city to very small asian tropical island in the middle of nowhere. Best decision ever.
I did got through the hassle and setting up a Thai company. This gives me a 1 year multiple entry visa and a work permit. Cost around 2.000 USD. An agency will handle the paper work for you.
It is a hassle no matter if you choose to do what i did or if you do the tourist visa, but it certainly is possible to stay and work for years in Thailand and many do although it is getting more difficult.
So yeah, it is possible to try to live here for a year on tourist visa, and if you fall in love with the place as I did, you have options in regards to make a life time stay and to get that work permit so you are legit.
I have been working remote from here for 6 years so far and counting )))