I threatened you people with this, and I even promised Ryan, so here we go.
The iPod nano and mini are made for the audiobook. Small, lightweight and unobtrusive in your pocket, these iPods are idea for the commuter. I get through about one disc a day going to and from work on the bus. I use an iPod mini, but plan to buy one of the new nanos as soon as I can afford one, just for audiobooks.
Encoding audiobooks for the iPod is fairly straightforward, and while it might seem complicated, it really isn’t. Here’s what you’ll need:
An audiobook on CD
A computer running Windows XP or Vista or Mac OS X.
iTunes
An iPod of some sort (but not the shuffle)
Why not the iPod shuffle? No screen. The shuffle is great for taking a jumbled mass of collected tracks and throwing them back at you in a random order, but for audiobooks? Not so great. Of course if you want to use one you may, just be certain to set it to sequential playback, rather than shuffle.
Okay! We’re ready to get started. Let’s talk about encoder settings for a moment. Spoken word doesn’t require the same bitrate as music does. The aural complexity of a single voice is nowhere near that of a track with a band and vocalist. So you can cut your bitrate down to at most 64k. I like 96k myself, but then I like to pretend I can hear the difference. You could also set the encoder to “mono”, because unless it’s a dramatisation with several actors you’re just listening to a guy talk into a microphone with no separation needed. Mono means your tracks will only need half as much space, too, so it’s a good way to go. I’m wasteful though, and I like going for full stereo. Your milage may vary.
The last thing you need to bear in mind is that iTunes and the iPod will not see your audiobook as an audiobook unless it’s in Apple’s AAC format. So under preferences, click the Advanced tab and select, “Importing”. You’ll probably want to turn off Error Correction and Play songs while importing or converting. These serve little function, and on Windows in particular, Error Correction can result in ultra-slow rips.
From the “Import Using” popup, choose “AAC” and from “Setting” choose “Custom”. Select your preferred bitrate and either stereo or mono, as you prefer. I use the VBR option, though I confess I haven’t done a comparison encode to see if it makes a difference. The other setting, “Optimize for Voice” should definitely be checked, regardless of the other settings. Click okay and then we’ll get on to the actual work.
Open your CD in iTunes. Select all the tracks and go to the Advanced menu and select, “Join Tracks”. This will rip the CD as one big file. Before importing you’ll want to check your tags. I’m an anal-retentive jerk when it comes to this. I set the tags as follows:
Artist: The author’s name (e.g. Douglas Adams)
Album Artist: The author’s name in reverse (e.g. Adams, Douglas)
Album: The book’s proper title (e.g. The Hitchhiker’s Guide to the Galaxy)
Composer: The author’s name again (e.g. Douglas Adams)
Track x of y: You can leave this blank, or you can use this as a way to number the discs. If your album has ten CDs, you could call Disc 01 track 1 of 10. Sensible?
Disc x of y: Redundant, but a more proper way to number the discs than using the Tracks fields.
Genre: Books & Spoken
That’s all the tag editing you’ll be doing for now. Click “Import CD” and let it do its thing. It’ll probably take ten or fifteen minutes per disc, so you can relax while it’s importing. Once you’ve got the whole kit and kaboodle imported you’re on to stage two of the tagging. Name each file thusly:
Book name Disc X (e.g. The Hitchhiker’s Guide to the Galaxy Disc 01). Shorten that as you will. HHGTTG 01 works as well. Play around until you find a naming convention which works well for you, and then stick with that.
As I said, I’m an anal-retentive jerk when it comes to tags, so I always always always fill out as much useful information as I can. Under the “Sorting” tab, I fill out the Sort Artist, Sort Album Artist and Sort Album tags. You’ve got to do these one by one, unfortunately. The two artist tags get the author’s name in reverse (e.g. Adams, Douglas) and the Sort Album tag gets the book’s release date, Star Trek style (e.g. 1979.10.19). This makes the book appear in chronological order in the list when browsing, if this is important to you. It is to me. 
Once you’ve got this information entered (or not, as you prefer) you will need to set two other tags. This should not be skipped. Select all the tracks and get info. Set “Remember Playback Position” and “Skip When Shuffling” to Yes, and click okay.
I like artwork even though I haven’t got an iPod that will show it, so I always add this. It’s purely optional. Amazon is (unsurprisingly) is an excellent source for book cover art.
The next step is the most important step. iTunes still doesn’t know to sort the files under Audiobooks, because the files’ extension is wrong. Select the entire book and delete it from the library. Tell it to keep the files. Hide iTunes and navigate to your iTunes directory. Open the folder containing the files and change the file extension from .m4a to .m4b. You should automate this if at all possible, because it can become quite tedious. If you’ve got good command line-fu, you can do a simple batch rename, or use a renamer app.
Now drag your files back to iTunes. They should now show up correctly in iTunes under the Audiobooks section. Move them to your iPod and you’ll see them showing up correctly under the Audiobooks heading under Music.
Aaaaand that’s about it. I think. Comments? Questions? Problems? Let me know!
