Just this week I started looking into similar ideas. At the moment I've been experimenting with a Wacom tablet and screen capture software... I looked up the Khan Academy methodology and started there.

But if anyone has recommendations for and iPad app that offers a shared whiteboard experience please let me know. We already use Skype on iPad as our sort of virtual office so that would be perfect.

Or... make one! We'll buy it!

Yeah, there's whiteboard apps. I want a shared whiteboard. Ideally at least 4 feet by 4 feet. The key feature is both parties can draw and erase and the marks appear on both boards. I'm pretty sure I could talk employers into buying one for the office and one for each remote worker, especially with the arbitrage opportunities around different housing costs. Also, in my experience video cameras trained on whiteboards seem not to work that well because of glare.