Yeah, I think you've outlined what I would consider a pretty good strategy. It is VERY analogous to the 'free to play' direction that MMOs are starting to take. Let anyone play levels 1-3 for free, run low level VTT sessions, and give them access to plenty of content in that level bracket for free (they already have tons of stuff of this ilk that has easily paid for itself already and can be written down as lost leaders).
I think what they really still need though is a more mass market presence for this kind of a 'new D&D for the 21st Century'. Putting Red Boxes in Target is not bad, but as corny as the old cartoon was it sure plastered the D&D name all over the place and if you had certain well-known actors who have made no secret of having played the game to do some voice acting for it? Hmmmm. Done reasonably well it could certainly suck in a bunch of mind share and grow the game.
Really I think if you look at what they have been doing and trying to do in the past couple years they really ARE moving in this direction. Not with blinding speed or no missteps but it seems to be within reach at least. If that platform, VTT, CB, AT, and a good online community and resources really materializes it could be leveraged to do some very nice things. And if WotC eventually can't manage to pull it off then someone will in some form.
WotC has no competition and doesn't understand software really well yet. I think they have made some strategic hiring decisions recently that will help with that issue.
Vote with your dollar. DDI sucks right now, so they don't get my money. Essentials is good, I'll buy it. I'm on the fence about Gamma World, I need to look into the CCG aspect more.
D&D as a brand could be managed better and has more potential, but I don't think its time to start the funeral dirge anytime soon.