I just finished listening to every song in my playlist at least once, putting stars [I use iTunes] next to them when possible. Now I'm slowly starring the rest of them. Once that is done I'll be able to make playlists much faster. The only downside to iTunes organization, for me is how it breaks up soundtracks into their constituent contributing bands.

zeros first, then ones

I use the file system to do my sorting for me. I have a directory called "Music." (Gee, how original!) Beneath it are two directories, one for stuff I've already backed up on CD-R or DVD-R, and one for stuff I haven't. Then, in each of those are directories that contain rough genre types (Rock, Classical, Dance,etc). Then, underneath the genre directory are directories for individual artists, then under that are directories for each different release for an artist. I try to put m3u files in each "album" but occasionally miss one.

I dislike pretty much every single media management app I've seen, so I just use the file system to navigate to whichever track/album I want to hear, and use the m3u file to start up Winamp. (This is on my computer, natch.) I also have an old Turtle Beach Audiotron, which can play stuff over the LAN from a Windows or Samba share, and that unfortunately does not use the hierarchical method of organization I have described, so I end up just scrolling through its indexed list of m3u files most of the time.

For my portable player, I have a separate directory of stuff for that, all of which is pulled from my main library. (My player is only 20GB, and I've got - well, a lot more than that in my collection.) I swap stuff in and out of the portable directory, and sync the player up to that.

The only downside to iTunes organization, for me is how it breaks up soundtracks into their constituent contributing bands.

sciurus: I haven't used iTunes for a while, but isn't that what the "Compilation" setting is for?

I use iTunes and sort by rating and genre. And play counts.

Its not perfect but I can usually find what I want when I want it.

I think I want to get a smaller iPod though to cut down on just the amount of stuff. My Unplayed folder has like 1800 songs in it.

I think you may already have your answer...

"I've about four categories of music that I want to keep straight:"

Consider using the rating system, which gives you up to 6 spaces (no rating, 1, 2, 3, 4, 5) of ratings, which with a smart playlist very easy to organize the way you want.

"1) Music I just downloaded that I liked a lot, and want to put into the regular rotation."

These are rated zero stars (or no rating), with a smart playlist called "Recently obtained" or "New Stuff" which looks for all music with zero stars. If a new song just grabs you, you can rate it with 1 star (or more)....

"2) Music I just downloaded that I'm not sure about, but I want to keep it in a holding area of music to maybe get into some day."

These become 1- or 2- star songs. A new smart playlist reads "Holding Area" which looks for songs with at least 1 star but no more than 2 stars.

"3) Music I love and want to hear all the time."

This is for songs that are 3 or 4 stars. Maybe "Current Faves" with for the smart playlist?

"4) Music I love but I'm kind of sick of, and only want to hear every now and then."

Oddly enough, 5 stars can work here. Songs that stand the test of time and maybe get played so often as to feel *too* familiar are probably good songs. Give them their props and title them appropriately in the smart playlist. "The All Stars" ;-)

The only other thing I would recommend is coming up with "genres" that work for you. Try using slashes (/) to subtitle your genre (Jazz/Latin, Blues/Delta, etc).

This is how I organize mine. Then I can use smart playlists to create moods or even "homework" listening sessions. Not in a pretenious way. I label a playlist as "The unheard" which is simply everything that has a play count of 0. And I have a playlist labeled "Good and popular" because it contains songs with high play counts and high rantings (4 or 5 stars only).

These are simple query playlists too. Someone smarter than myself could probably come up with some pretty cool playlists... All 4-star songs from between 1970 and 1979 labeled as funk or soul. Endless possibilities.

Anyway, my $.04

deadcow - I used to do that, and I liked it fine. I only started using iTunes with the greatest reluctance, and only because my wife started using it, and I wanted her to be able to approach my music collection in a format that was familiar to her. I like it ok, but sometimes I just browse the folders too.

terrapin - that would actually work great, and I've considered doing it. The only problem is that I like having a 1-5 rating of how much I actually like the song. So if I could have two star ratings per song I'd be in good shape.

or what fenriq said :)

I think your playcount can help you achieve that agropyron. If you really like it you probably play it often. Possibly.

Good luck!

I just dump everything in to iTunes and let it organize. Why do all that heavy lifting when there's a forklift sitting RIGHT THERE with the keys in it and everything?

I have a playlists of the most recently added songs, most listened to, never listened to and one that's more or less "stuff I'm listening to now in general".

Compilation setting?

I found it! Ooohh.

*sigh* I don't. It was too complicated, and I gave up in defeat and went back to buying cds.

I don't love iTunes, but it works better than most everything else, so I tolerate its quirks.

I don't have the volume you have agro, but I do have the same problem -- a lot of "temporary" stuff I would rather not have iTunes organize in any way. Usually my process is:
1) rip or download
2) test listen
3) tag
4) organize by artist folder and album folder (lots of stuff ends up in Orphan Tracks, though).

But I don't like to restart my play counts or lose star ratings, so I have to carefully reconnect the iTunes listing to the file once renamed and moved. Fortunately with 6+ it's a bit easier -- you can just do Get Info on a renamed track, answer "yes" for search, move to the apropos directory, then drag the MP3 from the old folder into the iTunes file dialog. This saves me steps!

I used to clean out stuff that I delete from iTunes but I don't always bother anymore, mainly because you can only clear a track listing from the library -- you can't create a playlist of missing tracks.

I was enthused about Songbird and, um, the other music app people were talking about a few months ago, but I haven't bothered really trying them out (buggy and slow, I've heard).

I know people love their WinAmp, but it doesn't have Party Shuffle, which I use 80% of the time.

Oh, and I use the stars the way they're supposed to, in order of favoriteness. I also have iTunes playlists marked "Fresh" for recently-added 3+ star songs, "Heavy" for 5+ play songs played in the last week, and a few similar riffs on those concepts. I have playlists for my favorite artists sorted by track plays, but I try not to let my nerdy OCD brain insist that the star ratings are visually sorted. ;-) I have playlists like "2005 Faves" sorted by play count, too. I really don't do theme playlists, except a few like "political", which I only use to find songs easily so I can drag them into shuffle.

I have a folder labelled "mp3s" (though it now includes .ogg, and thanks to you guys, a few .m4as). I have a subfolder called "sort" for any artist with more than two songs. Loose songs are in the folder within named after the artist, album rips are in a subfolder named after the album. Artists with only one song go into a separate folder called "loose". Downloads go into a folder called singles (as it was originally my high-rotation new and loose singles), including all YSIs; pending review and later filing (which tends to back up).

This works for me, because I tend to listen to stuff in album format. Otherwise, it takes 5 seconds to dig for whatever song I want. I've recently started using winamp's Media Library, which allows me to Alt+L and pull up my most recent tracks (which also allows sorting by # of times played, creating an effective and automatic Hit List), or all my music files, with a find-as-you-type, then shift-click for enqueue. Most of my time is consumes listening to all your YSIs, though. You crazy kids with your music.

I know people love their WinAmp, but it doesn't have Party Shuffle, which I use 80% of the time.

From here: Rather than merely a list of user-selected songs to be played in sequence, Party Shuffle is essentially a special shuffle mode that is both predictable (future songs are visible) and editable (the order can be easily manipulated in several ways).

Create a playlist, then randomize. Do NOT click "shuffle." Voila! This has been a Winamp feature since before the llama. Or does Party Shuffle do something else that the first three or so sites on google don't describe?

I've used this any number of times DJing Radio MeCha.

Since you asked...
New CDs are ripped then moved to the appropriate directories. Anything newly downloadacquired is verified, properly tagged, then moved to the appropriate directory.

Partition > Letter > Artist > YearTitle, i.e.
A-F
  C
    Covenant
      2002 Northern Light
      2006 Ritual Noise single
      2006 Skyshaper
etc.

I have too many albums to do anything else.

Since I never listen to anything rated lower than three stars, I wonder if I should reorganize my priorities and have 3-5 represent favorites, 2 stars represent so-so tracks that I'll listen to anyway, and 1 star represent anything I don't particularly want to hear again. Anyone else do that? How do you use the stars?

And how does Winamp's media library compare to iTunes? Does it have star ratings and smart playlists?

Do any of you actually have the year field filled out in the tags for most of your music? It isn't usually present for most of the things I download or populate from CDDB and I'm sure not gonna fill it all in.

I just chose 20 songs at random in my iTunes library and ALL of them had date info. I get all of my info from CDDB. I use iTunes on a Mac. Could that be the difference? I certainly don't add it manually.

Yup. All of them. iTunes is surprisingly good (if not always accurate) about this; otherwise I manually do it from the CD or google. My filing system doesn't work otherwise.

It's got Most Played and Never Played, now that I look at it. I don't "rate" my music, because different tracks suit different moods. I like the "Never Played" list, though, for things I neglect.

It's got a Top Rated pane, too, but I don't know how to rate songs yet. There's a MusicMagic Mix button I don't want to hit right now, because I'm broadcasting (I'm guessing it does a "Party Shuffle" of whatever songs are currently selected/available). Google gives me this page, which doesn't tell me much. Later, I'll try typing "Space" into the find-as-you-type box and see if hitting that button gives me a mix of space-related songs. Could be fun for making themed playlists.

I see now that right-clicking on a playlist entry brings up a "rate items" list with stars/asterisks at the very bottom. Like I said, not a feature I'd use, but it's there.

Cool fields under the "Local Media" menu: Audio, Video (yes, it does video, and I'm considering dropping WMP from regular usage between this and the clunky but functional VLC), Most Played, Recently Added (another one I didn't notice before, thanks for making me look into this), Recently Played (which is my own little last.fm), Never Played (like I said, I'll be using this) - though it looks more like "not recently played" which is still functional but misleading, Top Rated (what you're looking for, I think), and Playlists.

I just thought of something. Perhaps some people aren't aware that one can decide which columns of information to view in iTunes? Using EDIT > VIEW OPTIONS one can decide which information to view or not. But one doens't have to view that information to use it in a smart playlist query.

To view all the information you have on a particular track, click on a track and under FILE select GET INFO. (COMMAND + I for Mac users). In iTunes for Mac there are a number of buttons one can click for information on the track (Summary, Info, Options, lyrics & Artwork)

Maybe I am wrong about this, but just in case some folks aren't aware, there it is :)

For mileage may vary in Windows.