Automatically update iTunes Library?

Or, any other way to keep an iTunes library synced up with its music folder?

Let iTunes do all the behind-the-scenes housekeeping. Import your music into iTunes and let iTunes take care of managing the file names and directory structure.

I find I almost never have to go into the iTunes Music folder. I find all my music through iTunes. If I do need to find a particular file for some reason, I control-click on the track and choose "Show Song File". The music is very organized in iTunes and everything is easy to find, so I find there is no reason for me to go mucking around in the iTunes Music folder.

Yes, iTunes sharing is limited and that is most likely at least partly due to agreements with music rights holders to limit the copying of purchased music. Each iTunes only sees what is in its local default iTunes Music location and does not have access to playlists that appear over the network other than to play the tracks. All the making of playlists and burning of discs has to be done on the computer that physically has the music files.

Part of what you want can be accomplished by having multiple computers or user accounts use the same iTunes Library file. However, only one user at a time can use a library. So, this will not help you if your challenge involves multiple users using iTunes at the same time. If you just want to be able to access the same iTunes library from different locations one at a time, this may do the trick.

To have User B use User A's library file, the document called iTunes Library in User B's music folder should be an alias pointing to the library file on User A's account, rather than a actual library file on its own. I often use this approach, so I can manage my main music collection from a different computer. One limitation I've run into is that Airtunes does not work without dropouts in this configuration. Don't know if that would be a concern to you.

You can't have it both ways. You either have separate libraries and use sharing to listen to another user's music, or you use the same library as another user, with only one user at a time being able to access it.

Well, here is what you can do.
Go to iTunes preferences
click on advanced tab with the cog wheel
check the boxes that say to keep the folder organized

Mac Mini Mac OS X (10.4.4) Mine

I guess nobody is getting the idea ...
I'm sure there are thousands of people looking for a
solution like this, may involve automator, or folder
action applescript...but whatever it is, it needs to
happen!

I guess you'll have to be the one. Good luck.

I know what you mean, because I've just finished spending almost 6 hours trying to figure out how.. and I've figured it out enough for me.. it might be good enough for you too, and I don't make any guarantees (I'm doing this between 2 accounts on the same computer with the library on the external drive. - Your setup sounds significantly different)

1. I started iTunes to get the basic folder heirarchy, and copied that to the external drive (also set the music folder in perferences to use the external drive)
2. I deleted iTunes Music and both the library files from my user account
3. I made aliases of both the library files and put them (the aliases) in the iTunes folder in my user account
4. put the same aliases in the other user accounts I want to share the libraries (also set up the music folder being the one on the external drive)
5. So Far.. it works. We both can't have iTunes running or we get a locked error, but with fast user switching we can fix that quick enough.

Sharing playlists is great, but if I can freely listen to a song, why can't I freely put it on my iPod (or at least make it an option somehow)