You can get a re-entry permit at the airport on your way out. In my experience it takes 10-15 minutes but I try to fly off-peak times so you may want to allow a little more time.
I just got a new US passport. Takes about 2 weeks. The passport is 52 pages. I hadn't realized that was 'extra pages' it doesn't feel that way. It's pretty easy process. One oddity is that you have to use 3 websites
1) The actually application
2) Pay for the passport (some other US government website)
3) Pay for postage for the return of your passport. That site is in Thai. You can use google translate but I would recommend getting help from a Thai friend who "understands" the language.
I came when I was 40. I have been here 9 years I will be eligible for the retirement visa in a few months (yippie).
Basically to stay in Thailand long term you will need to
- get rich
- get married
- get a job
- get a kid
- be a volunteer
They've recently expanded the 'get a job' category to include technical people. I almost fit into the SMART category except the company work for is not publicly traded and it's unlikely they'll provide all the paperwork the Thai government requires.
So far I have had a few marriage visas (same wife 1.5 years), volunteer visa (1 year), work visa (1 year), a few covid extensions. The rest of the time (5.5 years) has been tourist visas.
You can only do two land border bounces per calendar year, but you can do as many by air as you like.
An immigration officer once told me an ED visa looks suspicious for a person 40+.. I think its a culture thing.
If I were in your shoes I would look at spending
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my time in Indonesia (Bali) and
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my time in Thailand. I am fond of Bali, but you may like any other city.
Technically you can get as many as you want. Some claim there is a limit, that really depends on the embassy that you use. I would definitely shop embassy (get a visa from one, then another etc). The METV is your best bet. They are valid for 6 months, but if you stamp-in on the last day of it's validity, it can be extended 3 more months giving you a total of 9 months.
When I was shopping for METV from Australia I found Brisbane and Melbourne were the friendliest embassies.. I think post covid Brisbane Thai Embassy is gone, not sure about Brisbane. Point is, different embassies have different policies.
If you are showing that you leave Thailand every so often, the Thai authorities won't care too much about you coming. They are more concerned about people who don't ever leave.
You're first long trip here will be the most confusing.. After you experience how things work, the visa process will make more sense... Thai authorities are goofy.
I have done back-to-back tourist visa for several years. In the past nine years I would estimate 60% of those are tourist visas. Many people in group say it's not possible but it seems to work for me.
If you are 50+ you can get a retirement visa. Otherwise habitual tourist visas. You can get multiple entry for either, this will save you a little hassle and a few dollars.