Here is an article from Macworld that I think nails this subject down pretty well:
http://www.macworld.com/article/136824/2008/11/audiobooks.html

George Carr wrote:
As Jordan and Steve described, I also join all the tracks before importing an audiobook CD, then make a playlist of all the CD's in the correct order. But I sometimes had a problem with regaining my place after stopping playback on my iPod.
The article above talk about making the joined files bookmarkable.
"One important thing to do: click on the Options tab, then, from the Remember Position menu, choose Yes. Click OK to save this information—this will let your iPod or iTunes keep your place when listening to a long file."
Somewhere on the web was a post explaining how to change the file extension of 
the audio files from .m4a to .m4b, in order to make the file completely 
bookmarkable, so this is the practise I now follow. Now the only time the iPod 
loses its place is after it has been connected to a computer (usually I 
recharge it from a wall socket), or if I connect the FM tuner. This may be 
different on a Mac, but when you change the file name a new file is created and 
you have to show iTunes where to find it. Kind of a PITA but preferable to have 
to fiddle with the iPod right when you are ready to drive somewhere, work out 
at the gym, etc. If anybody knows how to join all the individual CD files into 
a single monster file of the whole book, I would love !
 to know how to do that, since this is the way downloaded audiobooks are 
delivered and playback is almost completely trouble free.

George

-----Original Message-----
From: Computer Guys Discussion List [mailto:COMPUTERGUYS-
[email protected]] On Behalf Of b_s-wilk
Sent: Monday, July 27, 2009 11:02 AM
To: [email protected]
Subject: Re: [CGUYS] iTunes problem

I have loaded books on CDs into iTunes. Many of them have dozens or
even a hundred tracks on each CD, and a book might be 10 or 15 CDs
long. These audio files typically have a name like Track 1, Track 2,
and so on, there are no differentiating titles, up to 25 or 99. So
when I first loaded up a book I'd have 15 tracks called track 1, and
15 called track 2 and so on, and I quickly discovered that iTunes
could get confused about the order of these apparently identical
files.
With audio books I generally have no problem listening to them in
iTunes. On an iPod it's another story. I was listening to a collection
by Neil Gaiman, with 70+ chapters. On my iPod they were out of order,
but not in iTunes. I took the book and merged all of the chapters,
adding chapter markers. It was easy, but, sorry, I don't remember which
program I used, maybe QT pro, Garage Band, or Audacity. It played
correctly on the iPod that way, and I could select chapters. It's
possible, no, likely, that since I didn't RTFM for the iPod Touch, I
might have set it on Shuffle by mistake.


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