If I can add my contribution... I recently tried (like 2 weeks ago) to Update the RetroPie (I'm on 3B+ and had it since 2020 like you). I even had a message stating that my version (Stretch, I think I was on 3.8) was not supported anymore, but I still did it.
Unfortunately it took hours (building from source was the only option) and broke everything.
So I flashed and restarted from scratch (made a copy of my configs and bios/roms folder first), using latest image from the RetroPie website... now it looks like a charm but I need to redo all the custom setup I had. I use the configs backup only as a reference since configs parameters might have changed and didn't want to break things again.
I wish you luck :)