The Easiest Way Copy Songs Off your iPod
I recently got asked to copy some songs off an iPod because their computer had died and they'd just bought a new one, which obviously didn't have their songs and audio books on it. As far as I'm aware they were no backups. I've tried a few of the applications and methods to copy songs off of iPods before, but thought I would lay down the easiest way I have found to help anyone in the same boat.
Music and Videos
There are quite a few applications out there which claim to allow you to 'backup your iPod' but most of them (like Yet Another iPod Manager AKA Yamipod and SharePod) haven't been updated in a while and either didn't work for me, or didn't work with the later versions of the iPod (e.g. 3rd gen Nanos).
In the end, the easiest solution I've found is to use a copy of WinAmp. You only need the free version, you shouldn't need any plugins. Just download, run, connect your iPod, select the tracks, right-click and select 'copy to local media' and voila, job done. Note that you can set the location is copies to in the preferences (it defaults to your My Music folder).
Quick, simple and fairly painless.
Photos are another matter, for two reasons. One, I haven't found a free solution to copy them, all the software I've seen is shareware. Second, unless you selected the option to copy the originals over, you've probably only got thumbnails (small versions) of the images that are designed to be displayed on the small iPod screen and therefore don't need to be very big, so you may only get postage-stamp-size images even if you do retrieve them.
The main points are that you can copy your music and videos easily, but photos you'll need to pay for. Perhaps the best recommendation is it's much easier just to back up your music, videos, photos and anything else before you need to rely on your iPod. External hard drives are pretty cheap and you can get a few GB of storage online for free from a number of different providers, so make use of it and save yourself the agro.