Wow.. The "Program" model seems like it would work for a lot of things - diets, exercise, study... Thought about making it a platform?
A limitation of our current media-rich approach however is the cost of adapting content - we took a short term cheap, long term expensive approach... :)
Regardless, I like the site, though it sometimes gets a bit choppy on my old macbook pro. I think £50 might be a bit steep as an up-front cost - it almost put me off.
Also, have you considered doing an iphone app for the diary? I use some supposedly motion sensing app to wake me up with music. It doesn't work very well, but for your purposes I could easily see just thumping the phone when I notice I'm awake instead of having to look at a clock and remember a time.