Im working out my options about what to do to stay here. American citizen who entered on a 30 day permission to stay, and extended once for another 30 days. 

 

Can I extend a second time at immigration? 

 

If not, can I fly out of Thailand and then turn around and fly back in to restart another 30 day stay? 

You can only apply for one 30 day extension per entry to the country.

Unless you have a past history of doing back to back visa exempt entries you should not have a problem.

Why not do a border bounce.

More bullet proof.

Not saying flight out and return visa exempt would not work but thinking not best option.

If doing flight out and back option then spending some time out would be good idea .

When does your permit expire asking since visa exempt entry goes to 45 days from Oct 1.