iTyranny: Tell me why I don't like iTunes

I really like my ipod touch, but I can't stand the iTunes software: not intuitive, not flexible, not nice.

I've had a Palm IIIxe for the past 10 years, and I really liked the efficiency of it. But, its age was showing: I could no longer sync to my Win64-bit laptop at home, and even the receptionist at the doctor's office mentioned that it was so old-school. I didn't want an iPhone -- I already have a cell phone -- but the iPod Touch looked like a good replacement PDA. It installs most iPhone apps, has wireless networking and bluetooth, and replaces everything I need a PDA for.

So, now I'm using it, and like it. I'm still trying to get my old calendar off the Palm, but I went for the 32GB edition, and loaded a ton of mp3 music files onto it. I also check my Facebook and twitter on it, "play" Foursquare, and I signed up for online comics previews via Comixology. Great!

All good, right? No. The drawback is the iTunes software. For people who think Apple walks on water, I've got news: If you're a non-conformist then iTunes is not intuitive, not flexible and not nice. All I want to do is to load some of my 300GB of mp3s onto the iPod, but the iTunes software assumes a smaller collection, probably all purchased through iTunes. Also, each time I sync up at home or at work I get the following message:


Each time I see it I wonder if iTunes is going to blow away my iPod, or the files on my hard drive, or both?
Am I the only one who finds Apple software sometimes confusing?