How much storage are you actually using? You could just split it between the r230s and set up zfs replication in proxmox.

System76, Framework, even Dell officially supports Ubuntu in limited cases.

I’d just try a couple different distros and see which one has the fewest issues for you. If you like, you can pay for official support from Dell or Canonical. If you do identify an issue in a supported scenario (Ubuntu version + device model) they will actually help you troubleshoot and resolve the issue. RHEL is the same if you want to pay a bit more.

A wiki would be great, since it allows user contributions and a familiar interface.

Not necessarily mediawiki, though. Or maybe something that allows people to submit individual options in a category and vote on them.

Get it running and set it loose!

Yeah that might be it. Sddm is a display manager, you might be using it for your login screen.

You might be able to work around it by just setting the service to restart automatically, so that it comes up properly once a display is attached. But if you can, I would try reproducing it on a fresh and fully updated install, and open a bug report to the maintainers if you can. Linux developers generally try to make really sure their programs don’t crash like that.

Boot log/kernel/dmesg, X/Wayland/kde primarily. Been a long time since I’ve had to troubleshoot something like this so I don’t know the new kids on the block. Maybe upstart or dracut? Whatever manages the boot process now

That seems strange. What’s in the log?