One of my primary problems is that it seems like maybe iTunes is lame, at least when used in a Windows environment. But there are others that just seem like idiocy on Apple's part:
One of the default settings when you install the iPod software is for it to pull every song you have on iTunes onto the iPod! Since I had already dumped all my MP3s (about 18 gigs worth) into iTunes it took some random selection that would occupy the 6 gigs on my new iPod mini and started downloading it. It took me quite a while to figure out how to stop this, because there's no paper manual, and the CD was pretty much inaccessible because of the intense downloading procedure.
Next, there's the physical iPod itself, especially the glorius "clickwheel," which is made out by many to be God's gift to consumer electronics. Well, I found it to be totally unintuitive, and I'm not exactly a novice when it comes to pulling gadgets out of the box and messing with them until I figure them out, without looking at the directions. I have figured it out, but I just don't understand the hype.
Finally, I'm still having a problem with it that's greatly affecting my enjoyment of the thing and it's usability: I can't figure out how to use the "random" function within a playlist, only within the entire list of songs that are on the iPod. My friend, Linda, is also having this problem, according to her fiance. If anyone knows how to do this, and can explain it to me, I would be very grateful!