[Nicolai P. Zwar]

Have any of you ever had to re-import all your digital music files?

Not sure what you mean by “re-importing all your digital music files”… re-ripping them all from CD? God beware, thankfully not… that would be quite a mammoth project. But that’s not what you meant either.
Do you mean re-converting them into iTunes from a different format (so basically, iTunes creates new files from something), or simply pointing iTunes to the files and create a new library?

I do curate a large digital collection, it’s my main way to listen to music (my secondary way is my Qobuz subscription). I don’t really play CDs anymore. All my CDs are ripped, plus I have a sizeable portion of lossless/high-res digital downloads from Qobuz, Chandos, Hyperion, Berliner Philharmoniker, and, and and… and indeed, I still use iTunes to curate them, hence they are all in ALAC format.

So if you mean by re-importing just creating a new iTunes library, I’ve done that several times, yes, but it’s never been any work at all… I just point iTunes to the files (..\Music\ALAC), let it create a new library from those files… and that’s it. My music collection is in one folder called “music”, which contains all the music files, a few playlists I use, etc. If I ever change laptops or re-install iTunes, I just point it to the subfolder “Music/ALAC” and voila, I’m done. And I’ve got thousands of files and albums.

Here’s an image of my music folder as shown on a Windows PC (it’s on a QNAP NAS, but connected as a network drive to my PC).

ALAC is the main folder, which contains all the music files (and nothing else), and ALAC is the only folder iTunes has access to.
FLAC contains a few select FLAC albums (that are also in ALAC, that’s for testing FLAC/ALAC differences in certain systems), indexArtwork contains images for MinimServer, MP3 contains a few albums only available as MP3, like MONKEY ISLAND soundtracks from the games, integrity-Logs contains file checksums (for verification/checking), and Playlists contain playlists.

I don’t keep my music collection on the actual drive of my laptop… I try to keep hardly any actual files on the laptop. When I change to a new laptop or computer, all I have to do is install the programs I want to use and set up some personal settings. All my files will all be in place where I need them (cloud, NAS, connected drives, etc.), but not on the laptop itself. The only files on the laptop themselves tend to be temporary, if I do some specific editing.

Not sure what you mean by “custom tags”… does iTunes allow “custom tags”? (I know MP3Tag can insert any custom tag you want, but iTunes won’t read or touch them.)