A friend send me a laptop and claimed $100 insurance, I still had to pay a hefty sum for duties. Laptops care $300 locally and probably come with a Thai keyboard.
Its been a few years but I had to bring paperwork... a MUST.
Also, oddly, you will need to bring crisp brand new $20 USD bills. I don't recall if that was for the VT Immigration or the Thai Embassy but one of them is very fussy about the matter.
It's been a few years but I have gotten a Reentry permit from the immigration office, no appointment. I had to spend an hour or two.
I have never spent more than 15 minutes at the Airport immigration to get a reentry permit. The point is perhaps appointments are for groups of people to help avoid delays.
If your son is married to a Thai person they are eligible for a Marriage Visa. There is a lot of paperwork to complete. I think the hassle is worth it, to live in Thailand but I find the tourist visa is an easier option. Perhaps one day my luck will change and I will feel differently but that isn't today (or the past couple of years)..