Me thinks you don't understand iTunes. USE playlists. Don't ignore them.

If you have 50GB, its obvious you cant squeeze it onto a 30GB iPod. The answer is to use playlists.

The issue of duplicates is only relevant if you do, in fact, have duplicates. Different "versions" of songs are not duplicates.

Playlists are references to the actual song file much like an alias or short-cut referrs to the originial file.

I have several playlists where the same song resides (say, 80's music, easy listening, favorites). This doesnt mean that the song is in three times. (this can be confirmed by going to Version Tracker and downloading a utility that can rip-out songs from an iPod. Youll see, there are no duplicates).

For instance, I have over 100GB of tunes and a 40GB iPod. Lots of those albums contain only one or two songs that I want. One solution is to delete the "side b" tunes. But sometimes I might want to listen to them, or maybe someone else wants to listen to them. Whatever, I keep them all.

My solution is to grade all of the songs I know by filling in the "Group" ID tag with grading like "Group A", - "Group D".

I also use several other grading schemes for genres of music like "Space", "Techno", "Comedy".

Then, I use playlists religiously as the source of my iPods music. I synch only the playlists I want. In my case, all of my music that I have graded fits into my 40GB iPod with room to spare. Other tunes, that I dont listen to, but say my mother, brother, girlfriend listens to, still reside in iTunes but is not synchronized because of my system of using Playlists.

There really is no limit as to how you can use playlists, smart playlists (the playlists that look purple), and mp3 tags.

Enjoy

Thanks for the advice, it's definitely useful. You made me realize that I didn't explain a couple things in the email.

Typically, I listen to an entire album when I'm listening to music, especially on my iPod. So, I don't have too many playlists because they aren't going to help me find my music any faster.

Currently, I use a playlist I call "iPod" and automatically sync that with my iPod. It works fine, but I want a way to know if I've gone over my limit without having to plug in my iPod or if I have any duplicates. Also, if you are using regular (not smart) playlists, it is definitely possible to have the same file in the playlist twice. This was the main reason I was frustrated.

I've used the comments tag in conjunction with my songs in iTunes to specifically tag duplicate songs. From this, it is fairly simple to make a smart playlist that removes all of the duplicate songs from the playlist (search for Comments do not include "duplicate") or something like that. My library is only about 6.5 GB, though, so it may not be practical on a larger scale. Sorting the library by song name makes it fairly easy to spot duplicate songs; I'm not sure how easy it would be to set up an AppleScript to automate the process.

I'm not sure if that solution would work for you because of the size of your library, or your listening habits. But that's what I did to get my library into a 5 GB iPod back when I was using that one.

Also, if you double-click on your iPod playlist, it should say at the bottom of the window how much space the playlist takes. From that it's a simple matter to determine whether you've gone over your limit.

A couple points:

First, when you create a playlist the size of that playlist appears in the bottom of the iTunes window. This lets you know if your playlist will fit the iPod.

Admittedly, this isn't perfect. I actually use multiple iPod playlists - each iPod playlist startes with • to differentiate from non-iPod playlists. If a tune appears in more than one iPod playlist it's file size makes two appearances but the file itself gets placed on the iPod only once. In other words, I often wind up having more room on my iPod than I initially expect due to duplicates.

Second, read the last bit again again. If your playist duplicates a song it doesn't put that some on the iPod twice.

I'm not sure if you're synching your iPod with a Mac or a PC, but if it's a Mac you can use applescripts like those found at Doug's Applescripts for iTunes (www.malcolmadams.com/itunes/) to solve all of your problems. There are over 250 scripts -- many to perform library maintenance tasks like identifying and eliminating duplicates, etc. Highly recommended!

To clarify, a playlists are just lists referring to the "Library" of music.

I could have a song listed 10,000 times in 10,000 different playlists, yet it will only take up space of one song.

Playlists do not physically take up space, the library does.