Tom....I got a 60 day tourist visa approved by embassy in NYC over a weekend. Filed on Friday and received it Monday. Buy a full fare ticket for a duration withing the initial 60 days and cancel it and get a refund. It just has to be to leave Thailand. Then file for the 30 day extension while you are there. Real simple.
Regarding your passport picture and your last travel I would just make a copy of your passport with your last international trip and write "No International Travel since xx/xx/xx" and scan and upload.
I was covered by Etihad for Covid insurance requirement for Phuket sandbox. I also have Empire BC/BS in NY with an international rider but I still purchased World Nomad Insurance for my trip. God forbid something happens I want the hospital to say "This guy has great coverage. Pull out all the stops!" 😁