I have always chosen to get reentry permits at the immigration office near the airport ahead of my journey. They don’t expire until your permission to stay expires so….you can get it ahead of time. I never trusted getting it at the airport in Bangkok because extenuating circumstances might result in me having not enough time there.
Getting it at immigration before leaving town provides me with peace of mind and happiness when starting my actual journey….
Please examine your visa. Note the “enter by” date. If that date has passed….or if your anticipated reentry date is beyond the enter by date on the visa…you will need a reentry permit. Based on your post it appears that your visa will show an enter by date of March 2023 so you should be good without a reentry permit
Each IO has their own interpretation of the police orders. For example, come to Chiang Mai and see for yourself! We have to bend over backwards…. AND forwards sometimes. 😉
I’m on OA and have been here for nine years. I get extensions of stay every year. I find that easier than going back and applying for a new visa every two years. Fingerprints, doctors certificates, bank statements, visa fees, etc. all add up to more aggravation than doing annual extensions of stay. I have no issues with the insurance required as I too would be buying it anyway.
One might, however, consider coming in visa exempt then applying for a non imm O visa in country. Same funds in the bank requirement as OA but, for now, now insurance required. The insurance component may or may not change in the future in re O visas but in the off chance that it remains insurance free, we’ll, so much the better. If they change the rules and start required it….no harm done if you have it anyway.
Unless the IO provided you with a new 90day report slip to carry with your passport….( as some immigration offices have been reported to do) you will need to follow your origins timeline for filing your 90 day report. Check the due date on your slip……