There is no comfortable option in iTunes to transfer large e-books or documents to or from the iPod. Every time major features are missing a freeware author steps in and creates a free program that offers exactly this functionality.
Ipodlibrary is the freeware program that steps in this time. You can use it to add and remove all sorts of text documents to and from your iPod.
Please note that iPod Library is only compatible with third generation iPods, which makes it less usable than it has been when it was released in the year 2005. It is also not compatible with any iPod that got released after that time including iPod Touch or iPod Video.
Ipodlibrary is able to import txt, doc, lit and html documents avoiding the 1000 notes limit of the iPod (by setting some to inactive which means that they do not count against the limit). It keeps track of the position that you are currently at which makes it easy to continue reading at the position you stopped previously.
Update: Newer versions of the Apple iTunes software are now capable of synchronizing ebooks, documents and other files with the iPod. What you need to do is make those files available is to add them to your library in iTunes first. Apple iTunes may detect some of the ebooks on the computer automatically, while you need to add others manually. You can use the File > Add File to Library menu or Ctrl+0 for that.
Once you have added the documents and books to iTunes, it is time to connect your iPod to your computer. It should now be displayed under devices in the iTunes software. When you click on books a the top of the window you get the option to synchronize all books with the device, or only select ones. Depending on your selection, it may take a while until everything is transfered to the iPod.
Update: The iPodlibrary website is no longer available. The most recent version of the program, released in 2006, can still be downloaded from third-party download portals such as Softpedia.
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Ghacks is a technology news blog that was founded in 2005 by Martin Brinkmann. It has since then become one of the most popular tech news sites on the Internet with five authors and regular contributions from freelance writers.