I wish you the best. You might have a problem with your 19 year old son as far as getting a long term visa. He’s an adult and that could be an issue. Try to do most things on the Thai immigration website very early. You’re too young for a retirement visa and unless you marry a Thai man, a marriage visa isn’t going to happen. 50 years old is the age that they are looking for. I can only speak for Bangkok, my Thai citizen wife who is also a US citizen after I married her in Southern California 15 years ago. She kept dragging me to Thailand for our vacations and I fell in love with the people. I can share my thoughts. Get the idea about driving out of your head. Cabs are not expensive, the BTS trains are fast, on time, clean and inexpensive. They are elevated. (Speaking for Bangkok only kid) so I have a house in Huntington Beach just south of Long Beach. I commute to Bangkok a few times a year. My wife stays permanently in Bangkok and is always busy selling her clothes. We have a Condo next door to Fashion Island Mall, this enormous 3 block long Mall in Bangkok. BTS is right there for her travels all over Bangkok. There are two prices in Bangkok. A Farang price (you, me, westerners, tourists) and a Thai price. When we were hunting for a condo I called around and was quoted 18,000 baht. When my wife called she was quoted 9,000 baht. Same condo. So our rent is $258 USD per month. Modern condo, balcony, underground parking, dual AC. Sweet place. Electric is $28 per month running the AC on most days. So make a Thai friend to secure lower prices for yourself. I’am in California now until later this year. Stay safe.
probably barred? For a 2 day overstay..? No. He will pay 1,000 baht at the airport and no issues. We were as a couple 5 days late and paid 6,000 baht. No issues.
Never been asked. But cash is king. Credit cards with no transaction fee is how I pay for hotels. Last resort is a debit ATM. Most people convert their currency to baht after arriving. (Not at the airport because the rate is a bit higher). Convert enough for a couple days worth. You’ll find conversion places all over. Get some 100 baht bills for taxi cabs.