@Mark *******

yes. If you come exempt, your leaving flight needs to be within the initial 30 days. With the tourist visa, your departure flight will be within the initial 60 days. You can change the flight once you go through immigration. Or more correctly, once you have been granted an extension.

If you plan to be in Thailand that long, you will actually need to leave Thailand at least once. The 60 day tourist visa can be extended once, then you have to leave. You will need another tourist visa to re-enter. (Or enter visa exempt).

If you got the multi entry visa, you could do the same thing, but re enter on the same visa.

Elite visa is the least hassle. It is also the most expensive, and is basically a very long tourist visa.

Assuming you have a US passport, you do not need a visa. You can enter visa exempt for 30 days (may be more??). You DO however need to fill in the entry form online in order to enter. Name, passport, accommodation. Stuff like that. It takes about 10 minutes to fill out, but can be a pain if you get something wrong and have to start over. I actually filled mine in the airport after landing once, so it seems to get into the system fast.

How does one overstay for 30 days (or any length) unintentionally?

1500 USD is doable. That should cover rent, living expenses, food, and normal entertainment. If you are out drinking every night, you may need more.

My first trip, I didn't tell a soul except my parents that I was travelling to SE Asia (Hong Kong, Macau, Kuala Lumpur, Singapore, Phuket last minute).

I will be honest, I have been to Shanghai a few times, and I felt safer roaming about there at night than I did in most of the US cities I have roamed.

Yup! Now it is "yes" or "no" answers. 😅

(I have been a country hopping tourist since September.)

My airlines usually ask me for most of my SE Asian countries. So basically, wherever I travel in SE Asia, I have a flight leaving.