First, my Isles iCal schedule. Subscribe if you want. I update it each season, and go back and put in the scores of the games as they finish too. webcal://ical.mac.com/scott.coates/nyi.ics
Second, that is weird. Normally I'd suggest you are trying to put 1.5 GBs of music onto a 975 MB Shuffle, but if you can see them on the Shuffle in iTunes that's not it.
What about file format? Are these missing files in any different format than the rest of your library?
Anything else like that that might freak the Shuffle out? The songs have names with German characters or anything?
If you've got time, try this. Make a playlist of JUST the offending songs. Sync ONLY that playlist to the Shuffle and see if it plays any of them.
OH! Wait! What generation Shuffle is this?!?! There was a weird glitch in the older 1G shuffle (the gum-stick looking one) that wouldn't play certain files (I want to say AACs??). There was a reset app that fixed it.
EDIT: Looks like there is a
reset utility for both Generations of the Shuffle now.