How do I get iTunes to recognize audio books that is not bought on iTunes Store?
Remember, not all audiobooks have enhanced features. Make sure the enhanced features work on another player to help you troubleshoot whether the issue is really with iTunes or with the audiobook. For whatever reason, Apple has decided—in both iTunes and on the iPod—that a true audiobook must be in either Audible.com’s .aa format or in Apple’s .m4b Protected AAC format. Anything else, and it won’t show up in the Audiobooks menu. So, to get your audiobooks to show up there, you need to trick iTunes and your iPod into thinking the tracks are stored in that format. On Windows, this is easy enough to explain and understand, but the process is labor-intensive. You need to change the file extension for every track in the audiobook from .m4a to .m4b, and then play a few seconds of each track after renaming. I hope this works!! Sources: http://aldoblog.