Every once in a while I get asked for advice when one of my family purchases an iPod. Rather than put it in email yet again, I thought I'd post what I've been telling people lately.
First, get a cover for your iPod. While the body of the devices are pretty rugged, especially the iPod mini, the screen scratches easily. Mine is difficult to read right now and it's because I put the iPod in the same pocket as my keys, just once. That's all it took to get thoroughly scratched up. It doesn't matter what you get, as long as you can access the controls (get the right cover for your model of iPod).
Second, set up iTunes to record in MP3 format, not Apple's AAC. While Apple's format is better in lots of ways, MP3 files can be played on almost anything and you won't notice the difference in sound quality. iPods happen to be the best music player right now, but that may not be true in five or 10 years. Don't get tied to Apple.
Third, avoid collecting lots of music that has been "protected" with digital rights management. People have been so brainwashed by a constant barrage of propaganda about piracy that it isn't worth getting into an argument about it. Just trust me on this one, or read many people who argue this better. DRM isn't good for you, nor is it good for the record companies. The latter just don't realize it yet. That means, for the moment, buying most of your music in CD format and recording it yourself (check first that it isn't a "protected" CD) or spending your money on sites that give you more freedom. Magnatune and MP3tunes.com are good ones.
Fourth, if you have lots of kids and don't commute to work on trains, you won't get much chance to listen to it. The easiest way I've found to listen to the iPod in the car is with one of those cassette adapters. The difference between the £10 (or $10) ones and the £20 ones is noticeable. Spend a little extra.