IF you are coming back in to thailand ON or after May 1st you have to file the TDAC (Thailand Digital Arrival Card) via the online web-portal
It doesn't matter what way you're entering the country, free stamp, visa on arrival, visa, extension w/re-entry, ALL foreigners are required to file one.
You can do it from 3 days before your arrival date right down to the day you arrive here
you don't have to do ANY 90 day report because your 90 day reporting stops counting down when you exit the country and when you come back you NEXT 90 day report is due 89 days from the date you stamp in 🙂
YOU DO have to get back in time to apply for your next yearly extension (which has nothing to do with the 90 day reporting) and at most offices you can do that when you have 30 days or less left on your current stamp (so any time after May 23 or so)
As a rule that's how it's been, you have to take any "regular" extensions on the stamp you're here on before you can apply for an extension for a different reason
BUT
You should check with your immigration office,
a few started saying once you took the 30 day extension you couldn't get the 60 day visit thai family one (which is just a made up rule and not in writing anywhere)
AND
a few other ones started saying you can only get the 60 day visit family extension from a Non-Imm type visa, not a free stamp (visa exempt) or tourist visa entry
That's why I said CHECK with your office well before you go for the 30 day extension to see what's what where you're applying