Earlier quoted context omitted.
It's funny because the desktop syncing is probably the worst part of the ecosystem. They didn't even attempt to make it work on Linux (fine, its a niche, but they also actively made it more difficult for open source software to work with newer models) and iTunes for Windows is one of the crappiest pieces of software on Windows, and that's saying something.
I'd say desktop syncing is a really great part of the ecosystem, since it means that I can buy a new iPhone and be completely up and running again in less than an hour. Upgrading the software is a breeze, which is something you can't say about Nokia phones (last time I tried). I'd agree that iTunes on Windows sucks, but that's not too surprising given that they are running it inside of their cross-platform Objective…
First, it interrupts whatever I'm doing. I like to listen to audiobooks, and if I'm at my desk, I might plug my iPod in so I can charge it up, but I don't want to stop listening to what I'm listening to. But no, it stops everything and starts syncing.
Next, I need to jump through hoops to stop the syncing. iTunes starts up, and has to do it's thing. I can't just cancel the sync, I have to click through popups coming from iTunes to cancel the stupid sync before I can shut it down again.
And god forbid iTunes actually SYNC what you mark to sync! I hate installing it simply because if I do, I have to go find the place that says "Yes, when I tell you to sync an audiobook, you should, you know, actually sync the audiobook."
And then, after you are done syncing, I can't just jump back into listening to what I was listening to before.
Yes, this happens, it happens often. Really, the entire iPod/iTunes environment makes me regret getting the iPod.