Okay...Here goes.
I realized a long time ago, I was severely disorganized with my digital music. I'd download or rip an album, throw the folder in a long list and this was okay for awhile. Then I started branching away from VGM for a time, so now I needed to separate it from the influx of new music. No problem. Then I separated the heavy metal from everything else to help myself out. Then I started buying and ripping lots of domestic CD's and before long, I was completely overwhelmed. This was around 2011 or so, but it was a progressive issue (though a high quality problem to have).
My problem was three-fold: How to organize the albums after the regular/VGM split, how to properly tag everything and how to notate my favorite tracks from each album.
-Organizing takes on a life of its own. What genre does stuff belong to? Is ACDC classic rock or metal? I group my VGM by game genre, so some of the obscure stuff is hard to label. It's a constantly changing thing. At the same time, I want to make sure my subgroups aren't too large in and of themselves, otherwise it just becomes a pain. I tried grouping by company and that was a complete and total failure.
So for right now, I have this for VGM as far as folders:
Arrange Albums
Symphonic/Piano/Acoustic Arrange Albums (mentally, I've always had these separated from the regular rock/synth based arranges, so the folder split works well)
Game and Anime Vocal Collections (for stuff like Tokimeki Memorial, Sakura Wars, Slayers, Ranma, etc...I don't own enough of them to justify separating game/anime)
RPG Soundtracks (no explanation needed, although I tend to put some action-RPG's like Zelda in the "general" folder. I also personally don't count visual novels as RPG's.)
Fighting, Shmup and Racing Soundtracks (usually these are all short and straightforward types of soundtracks and I don't have a lot of any of them...I used to have shmups and fighters separate and racing soundtracks lumped in with "regular" soundtracks)
Falcom Albums (I like to keep these separate for a number of reasons - the sheer overall quantity, the high number of arranges that clutter up the regular arrange album folder, the fact that I know most of these by heart and because a lot of them define what 'ideal' VGM is to me. In other words, they've earned their own folder)
Soundtracks - General (for platformers and games I can't figure out what they are or where they should go. If there's ANY debate, the soundtrack goes here)
Retro and Boxsets (Boxsets usually cover many individual soundtracks, so it is good to keep them split up. It's also for stuff like the Famicom releases, that cover a bunch of soundtracks on 1 or 2 discs. I finally decided it was best to just tag everything with the boxset or release name instead of creating subfolders and tags for EVERYTHING within the boxset)
And I separate regular music like this:
Classical (this doesn't grow too much, it's mostly Bach/Mozart/Hayden stuff. Otherwise, I could probably separate it farther)
Pop/Rock (the bulk of my 80's stuff goes in here...It also includes stuff like eurodance and eurodisco, as I don't have enough to separate it out. Also has soundtracks that are just collections of songs)
Classic Rock
Heavy Metal (there's constant debates between 'classic rock' and 'heavy metal', but I tend to put stuff from the 70's in the classic rock folder even though I consider them metal. Chances are, if I'm looking for a metal album to listen to, I'm not searching for a Led Zeppelin or Rush album)
Country/Folk/Contemporary Christian Music (not a lot, but some artists release SO MANY ALBUMS, this folder became necessary)
Jpop and Seiyuu (my collection of these has gone up substantially, since they're so cheap, so I decided to group them off from the Game/Anime stuff. This also includes stuff like X-Japan, Show-ya, Princess Princess, Personz, etc)
-Tagging/naming. I'm a fan of the "artist - album (year)" format for folders. Within a folder, I always do "101, 102, 103" and so on, as opposed to individual subfolders for multiple discs. Having the large list benefits me, especially when it comes to labeling my favorite tracks from a release (see next part) and the fewer subfolders, the better. I have enough albums to flip through, cutting down on the number subfolders is one of the strongest benefits of going digital. Choosing which album to listen to is often a pain, but then you get to choosing which DISC of an album to listen to.
My tagging of regular albums is pretty standard. If it's a multiple artists album, I'll add the artist in paranthisees after the track name. However, for VGM and the "Artist" field, I put "(Game)" after the composer's name. This is so when I load a bunch of music in, I can still search for game music if the genre option is not available, as well as by artist (so I can search by both "Yasunori Mitsuda" and "Game" if I want Chrono Cross in the current playlist, for example). VGM, especially albums with multiple artists, can often be a pain to tag and credit properly, so often I just get lazy with this. The fewer artist names in the overall database, the better. I'm more interested in "does it sound good" and "can I find the damn thing?"
-Labeling favorites. One of my favorite things about my old iPod and iTunes was the option to assign star ratings to your favorite tracks. Amazingly, none of the players I've used since then have this option. And let's face it: Not every track on every release is a winner.
At one point, I was just deleting stuff I didn't like and I figure whatever is left is good. Then stuff happened...My listening tastes changes, my sound setups changed, the price of memory dropped like a rock and I was left with incomplete albums I had foolishly gutted. And then there's just the fact that even the good stuff varies in quality.
So finally, I started marking the track names of my favorites with a "$" symbol before the track name. This doesn't screw with the tags, I don't have to delete tracks if I don't want to (I only do it on CD's I actually own, since I can just re-rip if needed), I can search by the "$" symbol in whatever software I use and when I sort by name, all of the "$" tracks appear first and the untagged stuff stays at the bottom (this is why I prefer having only a single subfolder for multiple discs within an album). All I can say is it has taken all of the guesswork out of managing close to 1500 different albums and finding the tracks I want from each.
And for the albums themselves, I sort them by how much I like them by putting a tag prior to the album name. Again, this groups everything together when I sort by name. So I use:
(HQP) - short for "high quality problem", usually these are my favorites with few or no tracks deleted or not-favorited
(4) - great albums, sometimes they need trimming of some filler or crappy tracks done. Hey, they can't all be favorites.
(5) - generally good albums with various issues (poor mastering, crappy singer, etc) or a crappy album with 1-2 must-have songs. Either way, a notch below the other two categories.
(g) - short for "gutted". Garbage, lucky if it has 1 or 2 tracks worth saving. Sometimes I'll delete these, but sometimes I'll leave them around as a reminder so I don't re-download or re-rip the CD again.
So my Dracula Battle Perfect Selection looks like this:
(HQP) Dracula Battle Perfect Selection
$01 - Beginning
$02 - Bloody Tears
$03 - Ripe Seeds
...and so on.
So if I came back to Dracula Battle six months later and somehow forgot what the best tracks were, I can look and see. Obviously for albums where the quality of tracks jumps around, this is useful to have.
Needless to say, now that I've gotten the hang of managing my digital collection, it is a lot of fun to play around with.