I honestly think that if WoTC is going to continue making D&D, they need to get as far away from books as possible.
More miniatures, tiles, board games, and things that lead you online to the DDI.{/quote]
This bit I agree with
But then again, I think they need to make the DDI free as the character creator part and charge people for access to things like Dragon, Dungeon, VTT, etc... Getting people to make character to play your game should be something you want to encourage as much as possible, especially when you're going to be pulling that data to see what they're doing. Making a beta product and charging the customer for it while misleading them for months as to whats going on on the other hand...
This bit, not quite, Here I would make the VTT free but point to and provide via DDI lots of addons that make the VTT simple to use.
If I was to make the CB free then only for the first 3 levels or so and some free level 1 to 3 adventures, with an open ended story. Want to see the end sing up on DDI.
ALso if the VTT access is free and the initial level characters then one can run sponsored on line encounter type games for the uninitiated with some goodies redemable when they sign up.