Proxmox really helped in improving my homelab needs and I only really have about 10 apps hosted.

What is Trebel? Their page is very vague and doesn't really offer an explanation

TIL that Jonathan Bree, which I thought I only knew from his "You're so cool" single, sings with Princess Chelsea on this silly and wonderful song that I very much loved when I heard it 15 years ago
https://youtu.be/4TV_128Fz2g?is=gyI7J_yxQecggEEH

I't don't think it's supposed to be depressing but I wouldn't consider it happy music.

I know that my flow will not be for everyone.
I have a very similar experience to OP, but I quit Spotify more than three years ago.
For music "acquisition", I use bandcamp, qobuz and soulseek. Then stream it using Navidrome.
For music discovery, Bandcamp has weekly shows and I listen a couple of them. I listen to online radio during work, mainly NTS, KEXP, FluxFM, and SomaFM. I'm also subscribed to the KEXP channel on YouTube for live performances.

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!!!

I heard something similar regarding the outfits, but it was because they had 2 gigs in a row at the same bar and on the second night they decided to dress up to fool their friends

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.

Just thought I'd also comment that beets does not have a metadata index, it relies on Musicbrainz for metadata fetching. There are also plugins for other services like Bandcamp or Spotify.

You can use the https://beets.readthedocs.io/en/stable/plugins/lastgenre.html plugin to write genres