First, go and watch this.
Then go look at the rest of his blog. He gets added to the friends list even if he doesn't link to the Feline Theocracy.
We have an iPod. We also have a Rio Karma. The Karma's software is lightyears better than the iPod. I hate Apple. MP3 players are hard drives with a simple file structure, a program or two and a child-proof human-machine interface. Having written code for PCs, SGI machines, the Nintendo 64 and microcontrollers, I can tell you that this requires journeyman programming skills at best.
The iPod has an MS Outlook-like function. Calendar, contacts, task list and so on. MS Outlook is a simple database. You could reverse engineer the structure of the database with a text editor and some simple binary dump tools. Converting one database to another is a TRIVIAL ACTION. While it was advertised to be able to import your Outlook information onto itself, in reality, the iPod was utterly confused by the whole affair. I would have had more luck asking a cruciferous vegetable to display my Outlook calendar.
After endless hours on discussion boards, calling support and going to the Mac store, we gave up. By the way, the people at the Mac store are talented professionals who, with a little training, could get a job at Abercrombie and Fitch. As mannequins.
Since they use Macs, their primary talent is looking cool and bored and hip. You, the unwashed masses, walk into their store, see how cool and bored and hip they are and buy a Mac so that you, too, may someday be that cool. Macs are cool. They come in cool colors and shapes. People who use Macs are cool. The rest of us are not.