Playing Position with Audiobooks

Question

I am at wit's end--I cannot get my iPod shuffle to start playing an audiobook where I want it.
I have a G4 Powerbook and am using OS X 10.4.2 and iTunes 5.0.1 (4) with all current updates from Apple installed.
I have meticulously read the Audible iPod Shuffle User's guide at:
http://www.audible.com/adbl/site/deviceCenter/myDevices/appleIpodShuffle.jsp
and the Apple FAQ for playing audiobooks on the ipod shuffle at:
http://docs.info.apple.com/article.html?artnum=300558
Specifically, the bookmarks marking the place where the iPod should start playing the file do not seem to be synced between the iPod and iTunes. That is, neither iTunes nor the iPod seems to care where the other thinks the file should be started.
I saw the section in the Audible documentation that says that bookmarks are only set when you hit Pause on the Shuffle. Carefully hitting pause either on the iPod or in iTunes doesn't seem to make a difference in getting iTunes and the iPod to communicate.
I saw the section in both Apple's and Audible's documentation stating that bookmarks are not synced until a track plays to completion and transitions to a new track. This doesn't seem to make a difference, either.
I am aware that the bookmark is supposed to be synced to the one that's further along in the file. This doesn't seem to make a difference--moving the iTunes start-point early in the file and then trying to sync the iTunes bookmark to the iPod bookmark doesn't change the iTunes bookmark at all.
A separate issue is that when I press play after the iPod has been synced or turned off, it never starts playing. The LED turns green for about two seconds and then nothing happens. The audio only starts when I press play again.

Answer 1

I also use my 1GB Shuffle for listening to audio books from Audible. I use format 4 only, syncing through iTunes 4.9 (I've got 10.4 waiting in a box to be installed before I update to 5/6) on a PowerMac G5. I have installed the latest iPod update. I have observed the following behaviors:
* When turning off and restarting the Shuffle, the bookmark point can be anywhere from a few seconds to a few minutes ahead of where it should be. At one point I thought this might have been related to how long the Shuffle had been turned off for, but this turned out to be untrue. It just appears to be random.
* If I play any other files on the Shuffle before or after playing the audio book file, when I turn the Shuffle off and back on, the Shuffle will not remember the bookmark, but instead return to the bookmark in use before I played the audio book file. Additionally sometimes when I turn the Shuffle back on, it will return not to the audio book but to the same point it did the previous time I turned it on, on a completely different file. I'm not sure when this behavior occurs, but I know it will happen if the Shuffle is turned off while fast forwarding or rewinding (I have big fingers, and I have accidentally slipped the switch a few times while holding down the buttons).
* If I turn off the Shuffle while paused in the middle of the audio book, the same behavior as above will occur.
All in all, using the Shuffle for audio books has been a very frustrating experience. I do properly eject the shuffle after syncing, and in general the sync point on the Shuffle is correct the first time I sync. But on any subsequent listening, the above behaviors occur.
No amount of reformatting or resetting the Shuffle has helped. I came to this forum looking to see if anyone else is experiencing the same problems, and it appears that at least some people are seeing similar behavior. My conclusion is, then that there is a problem is how the Shuffle handles Audible files, at least on some Shuffles if not all.
I'm thinking about upgrading to one of the new iPods or a Nano, but I think I'll search those forums first to see if those have any similar problems.