You can’t convert from a OA to an O in Thailand. You would have to let the OA lapse and leave to re-enter visa exempt or buy a tourist visa to convert to O or buy a O prior to arrival.
If you stay in country for 90 consecutive days you must report to immigration. A DTV visa allows you to stay for 180 days (and with extreme difficulty perhaps 360) so you need to report your presence to immigration each 90 days.
Entirely possible if you’re from a country that allows visa exempt entry. Your profile suggests you are.
No one can confirm if it’s going to be without hassle as entry is up to an individual immigration officer. If they’re having a bad hair day then you might get questioned or at an extreme denied. The latter probably won’t be the case but it has happened.