I've got far too much music to fit on my iPod. I'm looking for a way to manage the iTunes library so that I can easily set up a list of the tunes that I want synced to the iPod, without having to go through the entire library to "uncheck" those I don't want.
... so what I did was to create a playlist in iTunes for the music I want in my iPhone and physically drag songs into that playlist; and then set my iTunes up so that when my iPhone is plugged in, only that playlist gets synched.
My complete music library is set up to sync when my 160 gig iPod Classic is plugged in.
My solution is similar to tilt's, but more semi-automated by using iTunes' "Smart Playlist" feature.
I've created several "Smart" Playlists within iTunes based on different criteria. I limit each smart playlist to 1GB. When I want to change the contents of one or more of these playlists I go into iTunes, select all of the songs in the smart playlist and delete them. iTunes then automatically instantly refreshes that smart playlist with new songs from my library (that meet the rules of the smart playlist).
In iTunes for my iPhone music sync, I select only those smart playlists for iPhone syncing and voila, the next sync automatically updates the playlists in my iPhone with the new songs.
This mimics the way my old 1GB 1st gen iPod works with the it's "autofill" option that would automatically change the songs from a selected playlist each time you synced.
