Finally fixed my wireless issues. For some reason the VM the controller was running on just wasn't playing nice and the APs couldn't reach it when on the wireless subnet.
Not entirely surprising since the VM was over 8 years old and was P2V'd at that time. The the physical server was probably 8 years old before that. That's a LOT of Debian upgrades to live through.
So new controller running on Ubuntu Server 20.04 and everything seems happy. Though I may still make a new controller on a RPi3 I have running RetroPi but never really use. And maybe a new RPi4 would be better for RetroPi anyway.
A bunch of technomancers in the fediverse. Keep it fairly clean please. This arcology is for all who wash up upon it's digital shore.