Fishy, I just switched from PC's to an MBP as well, so I can answer most of your questions. To get everything from your iTunes over to the MBP of legend correctly, simply go to your PC's iTunes, go to the File menu, click "Export Library". This will export an XML file to a location of your choosing. When I exported, it was about a 10mb file. Now, all this saves is your song ratings, playlists, etc. Not the actual songs. Then, copy your entire music folder over to your iPod. Also copy the XML file to that same folder on your iPod. So now, you have a folder with a list of the artists in your library, and a single XML file. On your Mac, simply go into iTunes, go to the file menu, click "Import", find that XML file we created earlier (with your iPod connected, obviously (oh, and don't let it update or autosync or do anyhting with your iPod as it will delete everything)) and select it. For me, this started iTunes automatically finding the music in the same folder as that XML file and importing it accordingly with cover art and all (I think...not entirely sure about that one. But you can always use iTunes to find the cover art thru iTMS if it didn't).
Now, with contacts, simply go to Outlook or whatever you use on the PC side, and batch export all your contacts as (industry standard) vCards. Put those on your handy-dandy iPod as well. Then, on the Mac, open "Address Book" and simply use the File menu to import those vCards. It will be seamless. Now, with your calendar issues, I can't help you. As I have never used Outlook and know of no industry standards calender file format. But I do notice on my Mac that iCal has an "Import" option, so there might be hope yet...I dunno.
I'm gonna instant-subscribe myself to this thread, so if you have any more questions you wanna run by me, let me know. Later.
