In an earlier piece I mentioned iTunes, which started me ranting about it. As a user, it's one of the least intutive pieces of software I've ever used. You pay dearly for every bit of knowledge you gain. And then they go and change the UI, and you have to find it all over again. To make it even worse, and hide the functionality behind bugs so you can never figure out what to do when you have two minutes before you have to leave and the thing you need isn't on your iPad.
Here's what I would say to him: Steve, iTunes is some shitty software. How about getting with it and straighten some of its shit out.