I honestly don’t have too much to back up, so I run one full backup job every Sunday for different directories I care about. They run a check on the directory and only back up any changes or new files. I don’t have the space to backup everything, so I only take the smaller stuff and most important. The backup software also allows live monitoring if I enable it, so some of my jobs I have that turned on since I didn’t see any reason not to. I reuse the NAS drives that report errors that I replace with new ones to save on money. So far, so good.

Backup software is Bvckup2, and reddit was a huge fan of it years ago, so I gave it a try. It was super cheap for a lifetime license at the time, and it’s super lightweight. Sorry, there is no Linux version.

I learned this the hard way as well… I did a big OS update on mine once and it broke almost every application running on it. Docker worked perfectly still. I transferred everything I could to Docker after that.

I currently use Navidrome as well, but I really don’t use smart playlists like that. For me, I use Symfonium on Android, which offers a ton of options and is incredible. In all my years of using a personal server to host music, this app has been the best by a lot. As for desktop apps, I don’t use them much, but when I do, I use Musicbee, which also offers unlimited customization if you’re willing to put time into it. It used to have a subsonic plug-in, but I have no idea if it’s still active. I just use the local file location and treat it as its own entity. If the subsonic plug-in still works, it may allow you to do what you want since everything seems possible in Musicbee from my experience.