Personally, I don't get all the fuss over Tablet PCs. I type faster than I can write, so why would I buy a Tablet?
As for sync'ing files, get a big USB key/drive and use Microsoft's briefcase function.
For syncing Outlook, I have a personal folder created on my Thinkpad, and bring over a whopping archive across our network each month that contains every email I've ever sent and received for the past two years. Basically, anything I can do in the office I can do on the road, and it's **** cool.