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Look here and here for some examples.

There are free utilities out there PodPlayer is one that I often use - it allows you to copy all of your MP3 files off of your iPod onto another PC and it renames the files back to their original names in the process. It also allows you to play the files off of the iPod through the PC. The program is an executable that doesn't require installation so you can keep it on the iPod and run it directly from there.

There is an excellent piece of free software out there that solves this problem. It's called PodPlayer, available at http://www.ipodsoft.com/index.php?/software/podpla yer/. According to the site the software was designed for playing your iPod on a computer without iTunes, but it has an excellent Extract feature that lets you browse your entire iPod library in a very similar style to iTunes, including browsing by Playlist. Then you just pick the songs you want and hit Extract to pull them off to another computer. The best part about this software? NO INSTALL. You just copy the single .exe to your iPod's disk, and when you're at someone's computer you plug in your iPod, run the .exe from Windows Explorer, and the program runs right off your iPod disk. Excellent software. Enjoy!

Your iPod does let you download music back to the PC. Copy the iPod_Control folder. It's hidden under Windows. Not sure about Mac.

You want the filenames to make sense? Use PodPlayer's integrated "extract" wizard. This also has the advantage of being able to play your music on-the-fly from a Windows PC without downloading the music first. Excellent tool. I have it set up on the right-click menu for my iPod (in autorun.inf), and I hook up my iPod and run the program whenever I'm at work. Charge and listen at the same time.

PodPlayer | SharePod

My two cents on this since I just converted the 17 disc Harry Potter to bookmarkable AAC. I used iTunes 4.9 to rip the CDs using the new Podcast "optimize for voice" preset. NOTE: Bigger files are supposed to be more skip prone and eat more battery life due to the way the hd & cache are handled so I kept my files to single chapters which were about 40 minutes each, encoded at 64kbps.

I used "Join Tracks" to gather each chapter into an individual file), but a few chapters were spread over 2 consecutive discs and I wanted to combine them, so I used mp4box (Windows, Linux, but not OS X) to losslessly concatenate the AAC files. I then manually used a hex editor to change the file type from "M4A " to "M4B " and changed the file extension from .m4a to .m4b and changed the genre from "Books & Spoken" to "Audiobook". (AFAIK the rename trick only works on Windows, while the hex editing also works on OS X) Created a Smart Playslist for the whole set of files and enjoyed.

A few more possibly useful links MarkAble (Windows only) is supposed to help automate the process I went through, but I'm not sure how it concatenates the files and wanted to learn, and the aforementioned Doug's Applescripts has Join Together (OS X only), but that requires QTPro and it is still not clear whether this is a lossless concatenation or not.

You don't get it.

No, YOU don't get it.

If you need iTunes to use an iPod, APPLE controls what goes on and comes off. Not me. Not you. ONLY Apple.

You DO NOT NEED ITUNES TO USE AN IPOD. On the Windows side of things you can use Anapod Explorer, YamiPod, ml_iPod for Winamp, iPod Agent, or ephPod to name a few. OSX users have choices as well. Furthermore, even if I use iTunes, how is Apple "controling" what I put on my iPod? I buy a CD. I rip it to MP3. I put it on my iPod. End of story. Where is the control? I assume you are referring to the fact that iTMS uses DRM'ed AAC, but the fact is I am in no way forced to use iTMS. iTMS != iTunes.

The fact that you can use it how you want is ONLY due to the fact that Apple lets you.

Um, yeah. I *can* use it how I want, thanks for pointing that out.

I'd never buy a music player where someone else controls the content.

Neither would I.

In an effort to be more informative than "there are already programs to get various web items onto it, like one that gets google news and outputs it onto the iPod when you sync it", I did some quick googling..

Googleget - Grabs Google News and syncs it onto your iPod. Looks great, can't wait to try it.

Many other iPod tools written in .NET for Windows (haven't found out if these are open-source, if so I'd love to try to port some of them to mono/gtk) available at iPodSoft -- I tried out a few of these and they look great.

And then there's the big list over a iPodLounge...

um, guys?

The iPod IS an ebook. It wouldn't take much to make it work. As a matter of fact, people are already using iPods to read text. Check out this sort-of eBook creator, or this iPod ebook creator.

I'm certain that Apple's IP-conscious designers are making it as difficult as they can to use the iPod as anything nearly like an ebook, but they can only do so much. And someday, non-powered nonvolatile eInk-like screens will be used instead of LCDs, which will make hacking a usable eBook screen a lot easier.

You could store ten of thousands of books on a low-end iPod.

iPod Agent (windows)

is iPodSoft mentioned? yes i am part of it and no i dont have the money/time to get the book myself.... :-( Working 2 jobs and school sucks.

For example, their compendium of software includes:

A workaround for EU volume limitation
Ripping, encoding and tagging recommendations.
A utility to mass export Outlook contacts
News and Weather syndication downloaders.
By far the best way to retrieve your MP3s (a utility that sits on your iPod itself and is executable over a network!)
The fantastic iPod Agent, which creates beautiful XML music lists as well as performing loads of useful functions

Every other area of the lounge is equally as exhaustive - from iTunes configuration (you can do amazing things with smart playlists!) to headphones and case reviews. Visit the site instead of buying a book.

(Oh, and I'm in no way involved with the Lounge other than being a fan.)