I have an ipod nano- software version 1.0.4 (7.41GB capacity).
Just downloaded latest itunes version 10.1.1.4 (I’m running windows XP SP3).
I’m gonna try to explain as clearly as I can what is happening, but this is confusing the heck out of me… I’ve not had this problem with syncing in the past. I don’t have much on my nano- I actually have over 6 GB free, so it’s not a space problem. I’ve been wrestling with this for about three hours now and I’m ready to pull all of my hair out! :mad: 
This morning I purchased two items from the itunes store, both audiobooks. They are visible in my itunes library under the “books” category (and also in the purchased category, so I know I really do own them). Both items are checked.
I connect my ipod and it shows up in itunes on the left side. I click on Thelma’s ipod.
On the summary screen, I check “Sync only checked songs and videos.” (My whole library won’t fit on the nano.)
On the music screen, there are a bunch of music things checked and all are currently residing correctly on my ipod. I don’t do anything to this screen.
I also skip movies, TV shows, and podcasts, and I currently do not want any of those on my nano- none of the ones in the library are checked.
I go to the books screen. There I see the two books I have purchased. One of the books is Brainwave Suite (which is actually music, but since it’s meditation music, itunes classified it as a book). The other book is David Rakoff’s Half Empty. Back in the general itunes window, I had earlier created two playlists, one called Brainwave, and the other called Rakoff. The Rakoff playlist contains the two of his books that were already on the nano, Don’t Get Too Comfortable and Fraud, and I add the new book Half Empty. The Brainwave playlist contains only the one item, Brainwave Suite.
Back to the books screen under Thelma’s ipod- I also check the boxes in front of these two playlists. Here is a screenshot:
This is where it gets weird and has me totally stumped!
When I hit sync, nothing happens. There is a flicker in the little horizontal “activity window” at the top of the big itunes window, but nothing happens in the section of itunes called Thelma’s ipod.
First of all, Brainwave Suite does NOT migrate to the nano, nor does the Brainwave playlist. It does not show up under Thelma’s ipod at all.
Second, as for Rakoff, at one point during the 1,012th iteration of my efforts to make this thing work, I had manually dragged the Rakoff playlist in the left column of itunes up to Thelma’s ipod and the playlist now appears listed there, but after I sync, only the two of Rakoff’s books that were ALREADY on the nano show up there (i.e., Half Empty is NOT in that playlist, but Don’t Get and Fraud ARE in the playlist and on the nano).
I tried manually dragging the Brainwave playlist up to Thelma’s ipod like I did with Rakoff playlist, but even though when I drag it there, a highlighted box appears with a “+” sign, the playlist, in fact, does not show up there.
In summary , I cannot get the two new books that I just purchased to show up on the nano, even though they are checked in the library. Furthermore, the Rakoff playlist does show up in itunes on the nano, but only with the two older books in it. Neither the Brainwave Suite NOR the Brainwave playlist show up in itunes under Thelma’s ipod.
Can anyone help me out here? Thanks.
ETA: I have rebooted, ejected, reconnected, etc. multiple times.
