I've got a music library with timestamps for created dates being >12 years ago (2011) but some of the files likely date back to ~2002 or 2003 when I was pirating stuff with Napster on my dad's PC and have been transferred from filesystem to backups back to filesystems... so on and so on, from grade/middle/high school to college and now adult life.
At some point keeping your files and directories organized becomes a part of your workflow (can likely be automated after an initial hump of tagging songs correctly), such that you can move between music applications with minimal work.
I've settled on still using MediaMonkey (now on version 5) locally on my windows machine, that has its local Music folder stored in dropbox. I then have a linux server in my basement that does an `rclone sync` job nightly going from dropbox to the server's local filesystem on pair of HDDs in a ZFS mirror pool. The server then runs plex locally, which I can access on just about any type of client with the PlexAmp app. There some valid reasons to not like plex, but one thing it does well is it doesn't modify the metadata of your files themselves, and you can set it to prefer the file metadata over its autofetched metadata for your albums.
Essentially if you keep your files and dirs cleanly organized from the get-go, it's pretty easy to then go try out other apps/services (free or OSS) that fit your needs. Some purists will tell you to use Foobar2K or Winamp, which I believe are still viable options. But that said, I think just ensuring your files stand the test of time will be more important than your application of choice you use to consume them.
At some point keeping your files and directories organized becomes a part of your workflow (can likely be automated after an initial hump of tagging songs correctly), such that you can move between music applications with minimal work.
I've settled on still using MediaMonkey (now on version 5) locally on my windows machine, that has its local Music folder stored in dropbox. I then have a linux server in my basement that does an `rclone sync` job nightly going from dropbox to the server's local filesystem on pair of HDDs in a ZFS mirror pool. The server then runs plex locally, which I can access on just about any type of client with the PlexAmp app. There some valid reasons to not like plex, but one thing it does well is it doesn't modify the metadata of your files themselves, and you can set it to prefer the file metadata over its autofetched metadata for your albums.
Essentially if you keep your files and dirs cleanly organized from the get-go, it's pretty easy to then go try out other apps/services (free or OSS) that fit your needs. Some purists will tell you to use Foobar2K or Winamp, which I believe are still viable options. But that said, I think just ensuring your files stand the test of time will be more important than your application of choice you use to consume them.