If you want MAC (SELinux or Apparmor) (which I highly recommend) then use Silverblue / CoreOS or even SUSE MicroOS

otherwise I use NixOS. (But like I said, I’m possibly looking into switching because of lacking MAC)

Nebula is what I am using

Decided on Davis (based on Baikal) for anyone stumbling over this later on.

Can’t do Nr. 3, but that’s fine for me at the Moment

Radicale is really cool, but it just wasn’t for mee. Too barebones. No GUI, no sharing.

Baikal was pretty nice.

Though if you want sharing, Davis is probably the best. It’s the same Server as Baikal but a different GUI.

Caddy and Rewrite / strip_prefix doesn’t work?

reverse Proxy based on the /homass and then internally strip the prefix from /homass/x to just /x ?

I have Pihole in a Proxmox LXC Container that does just that. Just Pihole. It is set to automatically restart.

All for that Reason that you just named.