This seems like a simple proposition, except that our iPods are mated to two different computers. Mine is mated to my Windows desktop machine, and Tara's to her tiBook. This complicated the operation, which in the end required about 2 hours of time, three different computers and some good luck on my part.
The first part of the operation took the most time, but was the simplest. This was the actual ripping of the CDs. I did this on my computers, using iTunes. Suspecting, correctly, that iTunes and the iPod would not treat these tracks as "audiobooks" but as standard music. So while I was ripping the tracks, I also created a playlist. This turned out to be good idea because iTunes decided to not put the disks into order in the library.
The tricky part was figuring out how to transfer the 174 separate mp3 files from a windows machine to a mac. Not being much of a mac expert, but knowing that OS X is built on top of a variant of BSD Unix, I guessed that I might be able to ftp the files. Therefore, the next step was going to have to be to transfer the files from my windows box to my Linux box.
Again, I got lucky in this. iTunes limits the size of the file names it creates. This limitation happened to turn the Gracenote supplied title of each of the disks into the same title - cutting of the disk number appended after the title of the book. This resulted in all of the files being placed in the same directory. This simplified the transfer to the Linux box to a simple copy that took about 5 minutes to complete.
This was where my trouble began. I discovered that my Linux box is currently configured to only allow anonymous ftp. Given the limited time I had to play with this, I didn't want to try to fix this or find the anonymous ftp area. Instead I confirmed that if I placed a tar file in my public_html directory I could grab it on the mac using the safari web browser, and it would be downloaded, and automatically expanded into a directory.
So the next step was to create a tar file that contained all of the mp3 files. Not knowing if the program on the mac that was unpacking the tar file could handle a compressed tar file, I left it uncompressed. (Besides, mp3 files are already fairly well compressed, so it wouldn't help much). I then loaded this tar file onto Tara's mac. For this operation I moved her computer into my office and connected it to the wired network so I could at least try to get 100 MBits per second.
The final part of the operation was fairly straight forward. I started iTunes on the mac, imported the files - although I had to delete the tar file before it would import all of the files, claiming that there wasn't enough disk space. I created a playlist on that iTunes as well, although the files were in the correct order. I then hooked up her iPod, and it synced the copy of Harry Potter and the Half Blood Prince as well as the two CDs she had ripped earlier in the day.
All in all, this wasn't too bad of an operation, but it could have been much easier, or much harder.