I'm sorry for taking so long to reply, but part of me didn't want to jump to another conclusion, and part of me just got side-tracked with other things.
Nevertheless (alwaysthemore) it seems the issue was with my router. A weird bug where wireless-to-wireless communication was failing. Most of my "servers" are wired and the router wasn't logging any errors, so the issue didn't present itself until (I assume) the reboot after the upgrade. Honestly, if I hadn't had to print on paper for the second time this year I'd probably still be scratching my head on this one. Once I couldn't hit the paper printer, it became obvious the problem was with the router, and a router reboot confirmed.
I apologize for not doing a better root cause analysis and taking up everyone's time. Good luck with figuring out what's wrong for anyone still having issues.
I am kind of the same boat, I had OctoPi/Print update a bit ago, had no issues with it, but my printer was unconnected for a month while I was doing some mods to it. Got it back up and logged into Octo checked for updates installed once of the Discord plugin's then ssh'ed into the box and updated the system. Since that it seems like the Wifi stack just pukes all over itself and won't comeback in a stately manor, it only happens when it starts a print and could be 5 to 30min into the print, if there is no printing going on then its just fine. I have not been able to do the wired check to see if that causes a recovery given how the pi is cased atm.
So did a little tinkering and added a cron job to the OctoPi box, it was set to ping my gateway every 2 minuets. Got that running did a few smaller prints ( under 2hrs ) and no issues. Where before every print the network would die. Then checking the log file I found that while the machine was idle at some point the network went down twice but came back up at some point which it had not done before.
So for giggles I threw a cron job on my PiHole to ping the Octopi box every 2 minuets so I have pings going both ways at this point. Checking the log I had not lost network connection over night. I am running some bigger prints today into tomorrow and I'll check the logs once they have completed.
That sounds like power management issues we observed on the wifi nic under Raspbian two or three years ago. Last I checked that had be fixed either in OctoPi or upstream (can't remember), but maybe it's come back now.
edit Back then when I think this was the solution:
Could someone observing this reliably check if sudo iwconfig wlan0 power off solves it for them? I haven't seen this myself and thus can't check.
I'll give it a shot after the printer finishes a print. Oddly I had an almost 24hr print no issues, then tinkering with some plug in's and it locked up.
I currently have a logitech HD webcam, connection to the Ender 3v2 with the power pin blocked and USB to ssd with a transcend 128gb ssd drive.