Well… FML. I got a wild idea and I ran
sudo systemctl enable docker.service
sudo systemctl enable containerd.service
Rebooted, experienced the same issues, and upon undoing that change by running
sudo systemctl disable docker.service
sudo systemctl disable containerd.service
and rebooting, seems to have resolved the issue… 3 reboots in a row and the docker service is starting properly, the containers are auto-starting, etc. I don’t know what caused the issue, but trying to force the auto-start, then disabling the auto-start resolved it. It’s unclear why… but it works. Which is both a relief and terrifying because not knowing why it’s fixed means I also don’t know why it was broken 