I'm about to try the same thing you went through. I tried to update a pi which hasn't seen any updates for the better part of like 5 years, and got errors saying I need to update from stretch. The update finished (with failures) and now the pi boots up the retropie screen, then powers down. So I have to update or else I can't even use the pi.
I have another pi in the house which is basically identical, so I'll be attempting a clean install of buster with the hopes that I don't lose functionality of my very- simplistic use of it. Mostly just watching video files in kodi from an external hdd, and a bunch of roms I can copy from the other pi.
I'll probably make copies of the config and rom folders before I download and flash the new retropie software. But I haven't done this for a few years and I hope it's as easy as it used to be. Any roadblocks you overcame that might help me would be appreciated. I didn't see you make a 'success!' post so I can only assume you got it figured out and are back in business.