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I'm not sure if there is an easy way to rip bought music back off an iPod or not...

Sharepod is what you are looking for.

I use Sharepod and it cannot be used on the new iPods because of the database lockdown. I have no inclination to use Linux, but using a 3rd party app that isn't bloated or doesn't need to be "installed" is what I want to do. You just copy the Sharepod folder to your iPod and run it from the iPod itself. The download is about 600k.

This is nothing but marketing guys. If jobs was so anti-drm, why is it still so difficult to get music or videos OFF of the ipod? The DRM can even stay on the tracks, just add something in itunes to export music from the actual device to the disk of the computer it is attached to. I understand that there are already programs out there to do this, but it shouldn't have to be like that. Also, look at how successful the itunes store has been. I have bought a total of about 3 cds in my entire life, but i've also purchased 5-6 songs from the itunes store. Why? Because its convenient at work. If jobs said to the record labels "either drop/relax the DRM, or we're going to pull your music from the store" then we might actually see something happen. Until then, this is just marketing.

I've been using Sharepod for 2 years now. I have NEVER used iTunes to put music on my iPod. Sharepod allows you to copy music to and from your iPod, create playlists and it runs off of your iPod so that you have it with you wherever you are.

I know this is somewhat off topic, but I see that there are ad-sense type ads on this discussion for software that allows you to get songs off of an iPod. Now, I know that slashdot wouldn't exist without advertising, however, in this case, the ads do clueless readers a disservice.

No one should have to pay to get their music off of their iPod. Hell, even Apple now has a page that explains how to do this without any additional software other than iTunes:

http://docs.info.apple.com/article.html?artnum=300 173

Also, there are plenty of free programs out there that do what the advertised programs do:

Windows:
http://www.ephpod.com/
http://www.sturm.net.nz/website.php?Section=iPod+P rograms&Page=SharePod

Mac:
http://www.ilinkpod.com/
http://fadingred.org/senuti/

I'm sure there are some for Linux as well, but I've yet to connect my iPod to Linux so I haven't ever looked for any.

http://www.sturm.net.nz/website.php?Section=iPod+P rograms&Page=SharePod

Other than the silly 'you can't replace the battery' issue (really, Apple, let's get with the 21st century here) and the lack of wifi, iPods are wonderful little devices that sync effortlessly and quickly and have an excellent software and hardware interface (the click wheel is clearly one of the best interfaces out there). You have choices ranging from the tiny little Shuffle through the 60 gb video iPod. Battery life has improved significantly from the first-generation units (14 hours for a nano, 20 hours for the 60 gb iPod). There are also hundreds of add-on products designed for them, including some very decent dockable sound systems and FM modulators, which just add to the appeal. Finally, the sheer 'coolness' of the simple physical design remains untouched.

Add to this the slick marketing and the ease of use of the iTunes store, and you have quite the phenomenon. Let's not blame Apple for DRM, btw. The push for DRM is a much more universal problem, and has more to do with the RIAA grasping at straws to prevent us from doing what we did 25 years ago without anyone imposing on us (taping our vinyl albums for use in our tape players) because they don't know how to deal with today's technology.

I look forward to seeing the next generation or two of iPods. Perhaps they'll gain the ability to function as FM receivers and directly record. Maybe we'll get the ability to pop in memory chips. Replaceable batteries, wifi (the iPod as the media center for your entire home... wow!). Whatever they come up with, I'm going to bet that Apple continues to redefine 'cool'.

To say nothing of how foolish it is to keep all that music on a device you can't plug into anyone's computer and effortlessly play without first having an obnoxious conversation about it.

I'd recommend that you take a look at SharePod.