My big problem is remote stuff. None of my users have aftermarket routers to easily manipulate their DNS. One has an android modem thing which is hot garbage. I'm using a combination of making their pi be their DHCP and one user is running on avahi.
Chrome, the people's browser of choice, really, really hates http so I'm putting them on my garbage ######.xyz domain. I had plans to one day deal with Https, just not this day. Locally I just use the domain for vaultwarden so the domain didn't matter. But if people are going to be using it then I'll have to get a more memorable one.
System updates have been a faff. I'm 'ssh'ing over tailscale. When tailscale updates it kicks me out, naturally. Which interrupts the session, naturally. Which stops the update, naturally. Also, it fucks up dkpg beyond what --configure -a can repair. I'll learn to update in background one day, or include tailscale in the unattended-upgrades. Honestly, I should put everything into unattended-upgrades.
Locally works as intended though, so that's nice. Everything also works for my fiancee and I remotely all as intended, which is also nice. My big project is coalescing what I've got into something rational. I'm on the make it good part of the "make it work > make it good" cycle.