Apple

I mostly interact with it through iTunes on Windows, which is sort of just sort of frozen in time and frustrating as hell to use (that's a whole other issue in and of itself), but even switching over to a Mac and trying to interact with my iPod just feels like a more irritating experience than it should be. Hell, most of the stuff I that I should be able to do on the iPod itself, just can't be done apparently and requires you hook it up to a PC/Mac. Simple things like just adding a song file, renaming a song name, adding it to an album, or adding a picture. Yeah, it's easier on a computer, but there shouldn't be any reason you can't have the same functionality on an iPod or iPad at this point. I dread having to add songs to my iPod anymore, because half the time it will just refuse to add it and I'll spend an hour or two trying to troubleshoot it to figure out what the problem is.