1

No, you cannot do that.

What you refer to isn't a visa anyway, but an exemption stamp for a 30 day stay. That can be extended in the last days of validity, only for 7 days at a fee of Baht 1,900 at any Immigration office within the country.

No, they will not ask to see your departure ticket.

If you overstay by 1 day there's no penalty. After that it's a per diem fine payable on departure - and you get an "overstayed" stamp in your passport. Not recommended, but not the end of the world either. Unless you have any problem with police for any reason at all after your validity runs out, then it's a major drama.

2

It's not a big deal anyway. There are lots of immigration offices around Thailand and you can extend your Exemption at any one of them, so it's only a matter of convenience whether you do it on arrival or during your last ~week in Thailand. There's no harm in asking to extend it immediately after you get it. They can only say no, in which case you just go get it done a few weeks later.

Thailand immigration themselves wont care about your status on entry. Traditionally, it's the airlines that enforce the rules and there is a small risk that you would be denied boarding in US unless you got an onward/return flight within the 30 days. But if you are only a few days over and flying back on the same airline they would probably ignore it. If you wanted to be 100% sure, you could get a (proper) visa in advance from an embassy in the US, which would cost you less than your extension and give you 60 days, as well as the guaranteed boarding.

3

#1, read the title!!

4

"I am traveling from the US to Bangkok then back out of Bangkok again."

*

With a US passport you can get a free Visa Exemption stamp in your passport good for 30 days.

Where are you going to right away from Bangkok? Is it to another country or just another city in Thailand?

If you are flying to another country the free Visa Exemption ends when you leave Thailand. Fly in again and you get another free 30 days. (Assuming you have a US passport.)

5

I did. Yes, so OP knows it's not a visa, but he's so confused about everything else I thought it wouldn't hurt to clarify that bit too. Is my reply wrong?

If he's coming from US I'd think his problem might be getting to board the kite in the first place without a visa or return within 30 days, but that's now been mentioned also.

6

Thanks for the input all, very helpful. I am not leaving until January so I will go ahead and mail my passport in and get the 60 day visa before I leave to avoid any potential hassle with the airlines. I am flying different airlines in and out. Also, I will be staying in Thailand only so no in and out and in again but that was good to know.