It seems to me that it would be hard to target users with such a wide 
range of experiences (beginner to expert). I'm not familiar with 
adaptive learning techniques, but if I'm a moderate level user, I 
wouldn't want to sit through too much beginner level stuff to get 
through to the more advanced levels.

As far as paying for a service. I think that most users would have to 
consume a lot of your product before they're willing to pay for 
something. Look at Michael Hartl's Rails Tutorial. He's giving away the 
content for a high quality book for free in order to generate a user 
base. If Railscasts had started out as a pay site, I don't think it 
would be as popular as it is today. But if Ryan Bates started doing 
advanced level episodes for pay today, then I'd probably sign up.

I guess when I'm hacking all day at the computer and I run into a 
problem, I'll be googling for quick answers and be unlikely to take time 
out for a involved tutorial. My brain expects short, quickly consumable 
information from the internet. When I want to learn something in depth, 
I still like a good book to take some time away from looking at a 
computer screen.

Good luck.

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