I agree, regular Non O and extension of stay could be a good options as Canadians still get a affidavit letter and don’t need to deposit the required 800K baht if you can meet the monthly income of 65K baht.
That’s not a visa extension, but a whole new product called “Extension of Stay”, which basically is a a permission to continue your stay in Thailand, -not a visa. We’ll put a point here anyway, because that’s not OP’s question.
I guess it only has to be visa exemption. You can’t extend any visas, only apply for a new one, but he probably has extended his stay with a border bounce and another visa exemption.
You probably did a border bounce to Cambodia to get another 60 days visa exemption. You can’t get a re-entry permit on a visa exemption, so you’ll only get another 60 days visa exemption when you re-enter from the US.
If this is your third entry on visa exemption within a short period of time, I personally would have considered to get a visa while I was back in the states.
Sorry for asking, but why don’t you just apply for a Non O visa before you go to Thailand?
It’s as simple as anything, just fill out the form electronically, upload your passport ID-page, take a photo and apply. You’ll probably have it in some days.
If you’re passed 50 years and have funds, have you considered to simply just apply for a Non O visa and extension of stay only based on this requirement?
If you’re applying based on the soft power options as muay Thai boxing you’ll need to get approved by a gym that can provide you the required documentation first.