You need to use land borders. If you use the land borders that visa run companies use, you can drive yourself and pay a fee at the border for the stamp. Or just go with the border run company. You can live in Thailand non-stop if you use land borders
any chance you can do a little break down of your expenses?
I'm really interested to know how you manage to spend 2000USD per month living in the sticks. I've stayed in the sticks before and it would be impossible for me to spend 2000 per month cause everything is so cheap out there. The only way I would be able to spend that amount of money is if I was the village ATM
the border run companies usually say the Thailand province that is on the border, not the province in the other country. All border run companies in Phuket advertise border runs from Phuket to Satun and Phuket to Ranong
A popular way to make money for retired guys in Thailand is to start a YouTube channel and talk about bar girls. Those channels do well cause old overweight men with blue balls enjoy watching that stuff