1). When I return, will they simply not stamp my passport at all or will they have to stamp it again with the same exit date as the original? I know that sounds redundant, but do they need to show that I’ve re-entered?
2). When I apply for the permit, do I need to show travel plans or can I make the plans after I have the permit (I’m the cautious type).
3). Is it possible to get a multiple-entry permit that will be valid when I go to get my extension or will I need to wait to get that?
Either could ask to see your onward ticket. The reason the airline asks is BECAUSE immigration could ask and if you didn’t have it your return trip cost would be on them. Beyond that, what Stuart said :-). You can go in right away, but have an appointment and your files obviously ready.
You can leave and return to get a new stamp then an extension. At that point, you can attempt to get a bank account to get a non-O visa. Depending upon where you are, this can be challenging. In Bangkok, it’s really rough. In Hua Hin and Pattaya, apparently not so much. Agents can also help. You can also try to do so now, but having a longer stay on your stamp helps. With an agent, you should have no problem if you go now.
Student visa will work if you’re going to stay put and honestly study. Everyone knows about studying Thai or Muay Thai, but there are many things one can study.
why take time out of his holiday sitting in immigration when he can get a tourist visa for 60 days if he plans ahead? Visa exempt with an extension is fine if one doesn’t have the 60-day visa for whatever reason.
Spend a night at a hotel…easy peasy. You need to go to immigration anyway, so choose one nearby. That way, you can be at immigration first thing in the morning too.
Very simply, no, but that doesn’t mean you can’t do as you propose. You certainly wouldn’t be the first (I had considered it). You just need to go home to get the visa.