I have a 60GB iPod w/color display. I had put the iPod down for awhile and didn't use it. Recently I started using it again and found some strange behavior with the syncing. I am using 7.3.2 version of iTunes on a Windows 2K machine.

Whether I choose the option to auto-sync or to manual load my iPod via iTunes I am having some issues. When I choose auto-sync, iTunes only loads about 145 of the 3500 songs that I have checked to sync (I have a smart playlist called All that I sync). I found it strange that my iPod synched so quickly because usually it takes forever.

I then tried to use the manual add method. I would drag playlists or songs to the iPod. I then clicked into the iPod to watch the sync process. As it turns out, the music appears to be syncing (it's grayed out) and then some of them just disappear w/o ever being loaded. (The ones that DO get loaded play fine when I eject the iPod)

I've tried to figure out if there's some rhyme or reason, but I can't seem to find a pattern. I get songs that I purchased off iTunes, protected or not, songs that I ripped myself (some were added to the library a long time ago, some recent, some played recently, some not).

I then tried using Red Chair software's iPod software. I am able to load all the music I want to, I don't have any issues with the music that would not sync and I can play and listen to the music. After the music is loaded, I can then start iTunes and I can see the music, change ratings, etc.

Red Chair is fine, but I'd really like to use iTunes so that I can manage my library. It's a pain to create playlists out of iTunes, export them and then import them with Red Chair.

Any ideas out there?