Should I switch to a Non-Immigrant O Visa or risk extending my current tourist visa in Thailand?

Whatever you're plan, I would have a plan B. Know which flight to KLA or PP you will take in case you're denied entry.

They have been cracking down, I guess. I *think* they're more concerned with people who come to Thailand and doing leave or don't leave enough. It sounds like you are here only part time. I think the Thai government appreciates those individuals who come to Thailand and spend money, then leave, then come back and spend more money.

If your plan is to go non o then just do it....

It sounds like you haven't been coming on any visa at all, because there was never such thing as a 30 day tourist visa. A tourist visa is something you apply for and pay for from the Thai embassy.

It sounds like you've been coming on visa exempt, which is when you arrive with no visa at all and you're from a qualifying country, and you get a free entry stamp.

You don't give any indication of how much time is between your entries so it's impossible to say. But even knowing that it would still be impossible to say since each entry is at the discretion of the officer you are standing in front of.

It's best if you can have the 3 proofs when you enter:

1) proof of funds (20,000 baht or equivalent in another major currency IN CASH ONLY)

2) proof of onward travel (a ticket out of Thailand within 60 days

3) proof of lodging (hotel reservation for at least a few days)

It's rare that you wouldn't get a warning first where they take you out of line and question you and warn you to get a visa next time. But being immediately denied does happen.