It’s unlikely that you can. With 60 day exemption plus 30 day extension then a border run you’ve covered almost 6 months. Keep doing that and you’re likely to be stopped.
Look at DTV. If you can get work online then you can do the ‘digital nomad’ thing
Not quite true. Some of us have had relationships with women we meet on dating sites. There have been a few that were only looking for money, looking to improve their lives and they weren’t bar girls.
I’m a similar age and have had some very good relationships. I now have a very sweet lady.
There are many Thai women that see farang as an opportunity to improve their lives. There are some that are looking for a loving relationship. It’s a bit of a minefield.