I don't think there is much to learn with the tablet. The learning curve isn't really steep at all. I think here's what you can expect:
1.) Take a few minutes (literally, only a few minutes) to get the feel of the pen on the screen. Use any ink-enabled program and just draw on the screen, and write a little. This is also a good time to calibrate the pen to make sure it goes where you want it to on the screen (a VERY simple, four-click process.)
2.) Learn your way around the TIP (Tablet Input Panel). That's your main interface, in many cases, between the pen and the software. Know how to open it, how to switch from handwriting to on-screen keyboard, etc. I bet anything you will be surprised at how accurate the handwriting recognition is. You DON'T have to learn any new strokes, like you do with a PDA. Just write normally (print or cursive.) I have bad handwriting, and it still gets about 95% of what I write. Others report near 100% recognition... without any training! (You don't have to train it.)
Once you've got those two steps down, you just use your apps as normal, but you've got a new tool --- the pen --- to enter text with.
After that, explore the following:
3.) Bells and whistles for tablets within each app. If you use MS Office, play around with the new ink capabilities. (Each app has an ink toolbar; you will probably have to turn it on the first time, as it does not show up by default.)
4.) Explore the ink-specific applications like Journal, OneNote, GoBinder, Franklin Covey TabletPlanner, etc. Explore the plug-ins for non-ink apps, like the Tablet Enhancements for Outlook, etc. Try out all the PwoerToys for Tablet PC's on the Microsoft site.
5.) Buy the book "Seize the Work Day: Using the Tablet PC to Take Total Control of Your Work and Meeting Day" by Michael Linenberger, which has become the Bible of tablet usage for new users. (Amazon's got it.) You don't have to be a business user of the tablet to get a LOT out of this book. Students will like it a lot, but so will casual tablet users.
Finally, the most important part:
6.) Report all your experiences and findings here on TabletPC Buzz. I love reading about new user experiences, and keep learning from other people who have had their Tablets far less time than I have. And if you run into any problems, this is a great place to find answers.