Who Knows When I'll Be Allowed to Enter Thailand?

No one, except Prayut and he's not talking. I can live with a 24-day quarantine, provided that I can spend it in Pattaya. I can produce the medical certificate and probably can meet the insurance benefit requirement, but when will planes be able to land in Bangkok?

Equally important, I know I can stay in  the country for 90 days. Can I apply for an extended visa at Jomtien Immigration as soon after landing and get it back before the 90 days are up?

I meant 14-day quarantine. BTW, I had an extended stay, 1 hyear, visa that expired in November of 2019 and couldn't return from the U.S. until this summer...

Hi, I think many hundreds of ex pats who normally live in the Kingdom but for whatever reason are not there now, but wanting to return as soon as the flights and airports return to near normal. But I am sure that they will require special insurance to cover much more than before, and of course some type of medical certification to confirm that you are clear but this clearance can probably only be accepted if is dated from a maximum of just a few days before flying out to Thailand.
I am also in that situation and happy to quarantine in my own home there if necessary. But I think clarity will come in the near future as to the requirements. 
Lets hope Expat.com will inform us all as to how we approach this next step in good time, as many things can get very confusing depending on your visa status and residential situation too not too mention some visas may have expired simply because we couldnt return earlier enough as all flights were suspended.
Kind regards.
John

It sounds like you should get an immigration lawyer to help

Yes, all the above. On the bright side my wife seems to be very happy and bearing up to life without 'grumpy old' pooah!.  And more so, you get better beer here, real ales, not just 5 brands of cat's p***.  Wine, good wine can be had from 300 baht upwards, and not just fruit juice adulterated with ethanol (or is it methanol?) so all is not bad. But I do want to go home to my lovely wife and son. 2 months away is 2 months too long.

Unfortunately, for us, there is very little, if any, logic applied. But patience is a virtue. When the country relies on tourism to feed its masses they're going to have to open the gate sometime. In the meantime we have to try and avoid the "grim reaper" He doesn't like old(er) men, and unfortunately I come under that category.

Just to add that I'm having the condo office send me a letter confirming my ownership of a con do in that building and a second letter from Bangkok Bank confirming I have over 1 million baht in  a SAVINGS account and have had over 1 million baht in that account for years. These letters hopefully would support my wish to be quarantined in my apartment in Jomtien