Look at the visa approval printout you got from the Thai embassy overseas, it will have an issue date and an expiry date 6 months later. What you want to do is make an entry before the expiry date to get another 60 day stamp that also qualifies for a 30 day extension. He can't apply for another Visa while the METV is still valid.
You will need to enter Thailand before the expiry date/enter before/valid until date written on the Visa to get another one year stamp. If you plan on leaving Thailand during that second year you will need to get a reentry permit to keep your stamp alive. If you're leaving on the 10th month and coming back 3 months later you can kiss your OA goodbye.
The flight information requested on the application is just intended/proposed itinerary. You're not bound by these dates and you can enter Thailand for one hour one day one week or 6 months. A departing ticket out is not necessary.
I don't believe there's anywhere where you can buy the one year non-O visa. I believe they have stopped selling that visa. You can buy a 90-day visa and then apply for the one-year extension in Thailand
Even though your job is fully remote it's a good idea to have a letter stating that you are authorized to work in Thailand and that you won't interact with any Thai businesses or individuals.
great, now all you need is to get the Thai court to officially recognize you. Stop by in a year and tell us how It's going as it winds its way through the system.