They don’t check whether you’ve done a 90 day report when leaving Thailand, so if you aren’t coming back then there will be no issue.
However if you are returning and at some point need to file a new 90 day report an eagle eyed officer may notice you failed to file a previous one and fine you for it.
With your Non O retirement visa it’s not possible to do a 90 day report as you can’t stay in Thailand for more than 90 days.
When you go to file for your year extension it is at that point the 90 days will start. Generally they’ll put a small piece of paper in your passport showing you when your first 90 day report will be due.
Be aware that after this extension renewals and 90 day reports are not linked. You do a 90 day report when you have been in Thailand for a consecutive 90 days and you do a renewal when it’s due.
A visa run is where you visit a Thai consulate somewhere and buy a new visa and then return. It’s not possible on the same day.
A “border bounce” is where you enter another country and either immediately return or sometime afterwards. This is possible the same day as there is no stipulation as to how long you would need to be out of Thailand for.
You will need a pen, your passport, a copy of your passport photo page, a copy of your entry stamp, a copy of your visa - if you had one and a passport sized photo. You fill out form TM7