I am surrounded by iPhones and iPods. My wife has an iPhone and one of my kids has an iPod Touch. And now our two youngest kids have "inherited" iPhones from relatives that have gone on to the latest iPhone model. (With no phone setup, they are effectively an iPod Touch with a camera.) Anyway, with all of that, I have seen a LOT of iTunes issues. We have had this discussion (thread title) several times with friends. I think it is a common aggrevation for most owners of these devices. And the question always comes back to "how is it that Apple, the company that is built on a reputation of ease of use, puts out something like this?" iTunes problems are never (rarely?) mentioned in iPhone or iPod reviews, and yet it interferes with all of your media and apps. You never know when a backup, sync, or update is going to go off into never-never land and not come back.
Being that my wife had to have the iPhone, we are now attached to AT&T at the hip. My first AT&T phone (a Windows system phone) died just after the Samsung Captivate came to market. I'm pretty happy with my Captivate and my wife is very jealous with the ease of synching. The easy blue-tooth & wireless toggles kind of get under her skin too. The added bonus is that I of course get to screw around with android programming.