When iPod was first released Apple was criticized for making it only possible to load songs onto it while at the iPod's home computer and seemingly impossible to move songs off of it, especially if you have a Mac, as there seemed to be no way to even see the files.
Two things have changed that make the iPod now even easier to move songs off of than a regular hard disk emulating MP3 player.
#1 is that the iPod will now work on either type of system if it is formatted on a Windows machine by simply hooking it up to a windows machine with iTunes and saying yes to the prompt asking if you want to run iPod update and wipe all the songs from the iPod (not the exact wording of the prompts, but you get the idea).
#2 is YamiPod, a free-ware product that allows you to read the iPod database.
This is the thing that makes me say it is now easier than coping songs from a regular MP3 player. With access to the database you can sort your files by artist, song title, album title, genre, play list, etc. just like on the iPod's interface, so you don't have to go hunting too far to find that track you wanted to leave on your other computer.
What's more is that YamiPod comes in both Mac and Windows versions that are ready to run straight off the iPod's hard disk. There is a Linux version as well, but it requires a tiny bit more effort to get it running.
If you are a Mac user you are probably thinking "Why would I want to take this to my buddy's place and format it for Windows?" Well, first off you won't lose any functionality by doing that, newer iPods use the Windows Fat32 format by default, in fact I'm not even sure you can change it. With an iPod formatted for Mac you are SOL if you want to use it attached to your buddy's machine or your PC at work. With it Windows formatted you can use it anywhere, because everything reads FAT32. Since you already have all of your songs on your Mac desktop in iTunes anyway you aren't going to really lose anything by formatting, you just won't have them on the iPod until you plug it back in at home and re-associate it with your iTunes to sync it all back up.
So now that I've hopefully gotten you over your fears about Windows-izing your iPod, let's go through this step by step.
#1 make sure your iPod is formatted for windows (just plug it into a windows machine with iTunes if you are unsure
#2 download YamiPod. You might as well get all 3 versions, you never know where you'll want to access your songs and it hardly takes any disk space.
#3 copy YamiPod to the iPod hard disk (if you can't find the iPod hard disk, go into the iTunes settings and make sure it is enabled for disk access there.)
#4 there is no #4, you are ready to roll. now all you do is plug into a computer that isn't the iPod's home computer, click on the disk drive that appears when iPod is connected and launch YamiPod from there. No install, nothing.
Easy wasn't it?