Wow. Just finished setting it up and tagged 2 álbuns. From slskd to Picard to Navidrome. This really makes my life easier.
Thank you very much kind stranger!!!

That makes a lot of sense and I also like the idea of having apps on the browser. I might take your approach to create a VM and spin it up whenever I need it. Thx.

Why docker though? The desktop app is available on all OS’s.

My experience is similar to a lot of people here. I see that we’ve all had our hurdles over the decades while moving OS’s and I’ve used many of the apps mentioned here (Windows/Linux). I couple of years ago i decide to stream my music because i was already into self-hosting and i really needed to properly tag my music for whatever server app I would use.
I always had my music structured by folder, i was using desktop apps for playback so it kinda worked for me. But i wanted to have better tagging. I had already used kid3 and picard but it lacked automation so I used beets for the albums on my collection (about 12K of songs). It wasn’t perfect but the software is not blame and it was a great way to tag automatically and move files for a consistent folder structure to match my needs.
Right now, since i don’t add music all the time ( a couple per week) i mainly stick to picard to tag new albums. it has 3 actions to manage the files on disk (move, rename, tag), I have script rules for naming files (if required) and i use the ReplayGain plugin. But I also have to point out that the learning curve of picard is rather high, the UI is a mess and it took me a really long time to understand how it works or where the options are.
After trying airsonic for a while i moved to Navidrome and have been using symfonium (android) and Feishin (desktop). It’s the best experience I’ve had since i started listening to music on my pc (199…6/7).
Regarding the source files, it lives on a disk and is backed up to another disk, managed on openmediavault.

This is how I started.
I have a dynamic IP and a router provided by my ISP. IP assignations, DHCP, are managed by the router. I went with DuckDNS for a free DNS service. Select a name and you get a myname.duckdns.org that you need to assign to your dynamic IP. duckdns has instructions to create a cronjob to update your dynamic IP on duckdns.org. (Routers come in all shapes and configs, chances are that this won’t work for most people) On the router, I assigned a static IP to the server hosting Jellyfin, in case of a reboot Jellyfin would always have the same IP. On the Ports page I opened up the default port for Jellyfin at that IP. I could then access Jellyfin outside of my local network using myname.duckdns.org:1234
This is not what I have right now, but it helped my get started.

What is MOTD?

I have a very similar setup. I work from home and use a tablet with symphonium for radio and my personal collection. When I’m in the car since I don’t have Android Auto, I just connect my phone with the Bluetooth. And I use tailscale as the VPN.

Great for self-hosting if its something you use. Not really a homelab thing, these two things are not necessarily the same either. My hosted services for the family are entirely segregated from my lab, which does a very different job.

My thoughts exactly. OP should look for something else to host on the homelab, there’s plenty out there.

Clever. I’m just starting to mess with Caddy. Been struggling with Vaultwarden lately and your solution might fit my needs.

I think this should be talked about more. Does every selfhosted app need to be public facing?
I use Immich as a backup service, so i really don’t have any need to have it public facing. It connects when I’m home. Same with contacts/calendar.