@Nick *********
it all comes down to how fast you can get your sh*t together, get those documents back, get the marriage registered, get the money in the bank and then go apply for the 90 day Non-O visa and still make sure you have at least 15 days left on your stamp.
EDITED as he used the chiang mai embassy for his freedom to marry document but lives in Surin Province (sorry I mis-understood)
SO there's a very good chance you'll either have to border bounce OR after you get the marriage registered take the 60 day visit family extension.
You're getting the cart WAY before the horse because until you get that marriage registered here you're dead in the water as far as marriage visas or visit family extensions