If you're used to Apple's program interface conventions, then iTunes is actually fairly easy to use. Problem is, Apple kept that interface on the PC version, when they should have re-written it from the ground up so it has a familiar "look and feel" of a Windows program.
That's not a problem; that's a strategy. If Apple can familiarize Windows users with their GUI by leveraging IPod users, that eases transition fears for switchover OS users.
As the Intel Macs hit the market, with dual-bootable machines, this may encourage people to ease into Macs. You'll be able to run the everyday productivity software in the Mac environment (word processing, mail, browsers, spreadsheets, graphics suites), then bop over to Windows for boutique/proprietary/legacy stuff and games. Then, if you want to mess with Unix stuff, you can do that as well.
I'm not used to Apple's stuff at all, and still think that iTunes is absolutely easy to use. Most every function can be accomplished with a click or two, or drag-and-drop. Redesigning the thing completely for Windows won't and shouldn't happen. They didn't do it with Quicktime, and no one complains about THAT program (at least, not its interface.)
iTunes is great. I'd rather use Winamp, but that's because I've been using it for 6 years: I'm under no illusions that Winamp is easier to use than iTunes.
I don't think Apple wants it to be "familiar" to Windows users. Their strategy might be to move the consumer to Macs.