Twice they pulled me aside. One at the airport and once at the Nong Kai border crossing. Both times they said "next time you come back...". They did not tell me "never come back", "you can not come in". I have an extensive questionable visa history and they still let me in.
I wouldn't stress it. If you have round trip tickets they'll likely let you in. They will likely not even talk to you, just stamp you in.
You said "we", if I were in your situation I was travel like normal, except when doing immigration. I send my travel companion through a different line, that way if one of you gets denied entry, the other can proceed, and its not a total loss.
But if you qualify and if it's not a financial strain, why not get the visa?
Pay some high school kid to figure it out for you. I just finished my eVisa (Thai Embassy USA), it's a pain but it's a lot easier than going to the the embassy. If you do not have the computer skills (which is understandable) hire a kid who does have the necessary skills. Honestly, about the only difficult thing was making sure I had the correct file types.
Bali would be my first answer. In the tourist districts it kinda sucks but if you find the AirBnB's just outside of the tourist districts it's quite reasonably priced. Once you get familiar with the place you'll find other places (Lombok, Gili, etc).
What do you need? I wouldn't consider myself a "good IT person" but I have been doing computer engineering for the past 20 years. I wouldn't know how to set-up a wireless printer but I can stand-up a network of servers.
I don't know that you did - I googled it but lost interest. I have, in the past, consider border crossing and Koh Lipe and wondered if land rules applied.
You can get a fresh stamp at (or before) December 5th, allowing you to stay until about March 5.
With the METV which is has a validity of 6 months and an expiration of 6 months its best to apply for it near when you will travel (3 weeks before), accept it won't be valid as long as you would like (6 months).
I bough/financed my condo. That was done privately through an acquaintance. I found no financing options but I did find individual sellers who were willing to finance. I think if you want to finance you will need to reach out to individual sellers. Hence, you're looking for a house that costs xxx and the owner is willing to finance (which means the sellers is getting a premium).
"As of June 7, 2024, the US prime rate is 8.50%"
5% home financing maybe a bit low. If you're financing you may want to wait a year or two.