I’m no expert, but I just put my first netlibrary book on my clip last week. I had a few problems, like I couldn’t get mediamonkey to transfer it, and when I first used windows media player to transfer it it wouldn’t play. What I did then was actually play it first with wmp to make sure wmp had downloaded the correct license. Once I had done that I was able to transfer it again and it played on the clip. The other thing I did was change the genre tag to audiobooks so it would be able to use the new bookmark features of the newest clip firmware.
I agree with what rdow wrote. It is imperative that you are in MTP mode so the DRM license gets transferred over. I also have to play the NetLibrary books on my PC to check out the license before syncing them to the Clip. I think they do this so that you don’t have to download the book again if the book expires. You simply check it out again on the NetLibrary website, play it with WMP to update the licence, and then re-sync to the Clip. If you use WMP to sync then all files end up under the “Music” folder on the Clip and you cannot change this. Not sure how MediaMonkey handles syncs in regards to where it ends up on the Clip.
By changing the genre to “Audiobook” (or “Podcast” ) - without an “S” at the end - the file gets added to the “Audiobooks” (or “Podcasts” ) part of the Clip under “Menu” … “Music” … “Audiobooks” (or “Podcasts” ), the 9th (or 8th) item on the list on my Clip. These “Audiobooks” (and “Podcasts” ) options only show up with firmware 01.01.29 which is awesome for us audiobook/podcast listeners. Make sure you upgrade to 01.01.29 to take advantage of bookmarking so you can go off to listen to music while you run or work out and then get back to your audiobook/podcast right where you left off (choose “Resume Playback” ).
I’ve also noticed that the tags for NetLibrary files make the books show up as “Unknown” under “Audiobooks” unless you edit the “Album” ID3 tag to reflect the book title. In fact it’s not a bad idea to check the tags before syncing to the Clip so you don’t have to redo everything. Hope this helps.