I keep a Los Angeles address and a Bangkok Condo. I use REMITLY to transfer from my personal California bank account directly into my Thai debit card account. I use a international credit card that has no conversion fees, paid for out of my United States bank account. I charge everything. There is no income stream to speak off. No payroll, no job. I doubt much could be made of it.
To keep up with Visa news and coming changes get subscribed to ASEAN ….email notifications. They discuss the latest Thai proposals on various visas and new rules. For instance you arrived recently with a 30 day exempt but soon that will change to 60 day on arrival. You’ll still have to go to immigration to get another 30 which will waste most of your day.
I would say yes. Get it over with early. Keep a small amount floating and use the debit card they give you. Keep aware of the fee structure every month.
Sir. Anytime now you’ll get a 60 day on arrival, then you can hit up immigration for the 30 day. 90 total. No exit and reentry needed. We’re just waiting patiently.