I've had one of these 160Gb Classic iPods for a month now.
iPods are designed to work with iTunes which is free and easy to use IMO. If you get stuck you can easily read up support
HERE...
To be honest I'm a bit disappointed with mine...(used on my Mac)
1. I've got 100Gb of stuff on it and it has a VERY laggy interface. It can take up to about 20 seconds to play a song you've selected...navigating can be like trying to run through treacle.
2. There has already been 3 updates for this model and the problems still persist but it's getting slightly better. I've formatted it twice and re-synced it (taking hours) problem is still there.
3. Photo slideshow music still doesn't play properly.
4. They changed the video output for this model slightly so no video accessories work with it anymore (like the ones I've already got...)
5. It takes about 60 seconds or more to mount/unmount the iPod after syncing- TOOO SLOWW
6. It is way too fussy about the type of video you can put on it, HAS to be H.264 format, even Apple's own Quicktime doesn't work. It took 3 days solid to convert all my videos
7. Functionality on the previous model iPod has been removed from this one when docked with my iPod Hi-Fi (which is very good) for some strange reason.
Unless you really need 160Gb of capacity I'd stay away from this model...I think the internal drive must spin at 1rpm which is why it's go laggy
Maybe stick with a flash-based iPod, i.e. Shuffle, Nano, Touch.