Many offices now allow people to apply during the last 45 days of their stay for a new Extension of Stay based on being over 50 years of age, the old regulation was during the last 30 days.
In you case if your current Extension runs out of Dec 27 you can apply starting 28 Nov for sure and maybe as early as 13 Nov.
Why would you not extend your marriage visa now? What if the Extension of Stay based on being unable to travel due to Covid (landborders are open) get denied?
What do you mean with a marriage visa?
Is that the Non Immigrant O visa based on being married to a Thai National OR the Extension of Stay based on being married to a Thai National?
NO, if you are on an Extension of Stay and use a re-entry permit you will get stamped in to the same date as your permitted up to xx/xx/xx already in the passport.
Alternative: Leave without a Re-entry permit and start all over again with buying a NEW Non Immigrant O-A visa before you make your way into Thailand.
Based on the data provided you will be stamped in until 1 Oct 2022 and have than 2 weeks to apply for a new 1 year Extension of Stay as insurance is already in place.
Hope your tickets are good and your passport has enough validity, safe travels.
When the Non Immigrant B visa is stamped in your passport you also get 90 days to stay inside Thailand. After 60 days you return to the Immigration Office with document of your employer and apply for the 1 year Extension of Stay based on Employment.
And 30 days before that years ends you visit Immigration again with documents and apply for a new 1 year Extension of Stay and keep on doing this as long as you work for this school.
If you need to travel, you apply for or a Single or a Multiple Re-Entry Permit.
You can do this directly after the Immigration Officer stamped the 1 year Extension of Stay inside the passport.