Can I renew my Non-O retirement visa and obtain a re-entry permit simultaneously in Thailand?

Your 90 day reporting only resets to day 1 when you re-enter the country

You would apply for the year extension and once they stamp it into your passport you would then apply for the re-entry permit

At Chaengwattana in Bangkok you get the year extension issued in Section L-1 and you buy a re-entry permit in Section C-2, so two different sections.

Once you get the new extension inked in and your passport back from section L-1, go down and make a copy of the data page of your passport, your new extension, your most recent entry stamp to thailand, fill out the Tm-8 re-entry application and get a queue for Section C-2..