One of the things that has bugged me a bit is trying to get my iPod and iTunes to work together as I would expect them to. At work, I've got a macbook that I use a bit, and one day I decided to plug my iPod in and listen to music via the headphones in the macbook. This turned out to be a surprisingly annoying proposition.
First off, you have to enable manual management of music and videos. This is probably the most baffling part of the whole thing, in that I have no intention of managing anything. As a bonus, whenever I resync my iPod at home, for whatever reason, the manual management flag turns itself back off. Next, you have to go into the music interface for the iPod. You can't use the iPod itself and simply stream the music into your computer, and instead you have a menu which is about one step beyond what we had in '95--a list of all your songs. You can't shuffle or repeat or see the album art or limit play to a single album. You must listen to all your songs in order as sorted. At least you can control the sort order.
The comedy of all this is how astonishingly clumsy it is, given every bit of it is Apple hardware and software. Usually the Apple experience is clean and just works exactly how you'd expect it to, yet here they've dropped the ball pretty badly.
As a bonus: I can plug my iPod into my ubuntu 10.04 machine, and it pops up in Rythymbox like magic. I believe the prior version couldn't read the iPod Touch, but the latest works great. All the things I want, it just does, with the minor exception of a lack of album art. How I suffer. Have I mentioned how ubuntu is turning linux into a great OS?