Flights of fancy are pretty much all we have to go with on this topic (mostly), but I do think some guesses make more sense than others.
Virtual Tabletop: I personally think any VTT plans are dead, D.. E.. A.. D.., dead. That was part of the original DDI strategy as it was announced during the run-up to the 4E release. That strategy failed almost completely; it was farmed out to an outside developer (like the old 3E digital strategy that also failed pretty badly), and those devs have been out of the picture for some time. I will honestly be surprised if any remainders of that stuff ever see the light of day. WotC would be better off making a new DDI virtual table project a lower priority than it was originally (and I think that have). But hey, that
would be an interesting surprise.
More Adventure Tools: After the consultants working the original application strategy failed to deliver, a new .NET applications team was built in-house. These folks have some real chops (or at least
had, depending on layoff impacts). The Character Builder is not perfect, but it's by far the most effective D&D chargen software
evar. I believe it was this same team that posted some throw-away javascript tools on the website for encounter planning. These spare-time widgets turn out to be hugely popular, and someone at WotC finally figured out this is the sort of stuff they should really be spending their time on. Between the Compendium, CB, and Monster Builder, they now have a pretty strong codebase to work from, and I think even a small team could maintain some momentum extending Adventure Tools in the expected ways. Which would make that no surprise at all.
Cross-Platform: I expect WotC to announce Silverlight versions of the DDI apps sometime in the next two years. Maybe even this summer. Future versions of the CB will be running in a browser on PCs, Macs, or any other platform Silverlight finds it way on. It's just a matter of time.
Regarding imaginary backseat driving with DDI revenue: please consider that subscription revenue has to first offset any lost book sales before anyone starts rolling around in piles of cash and funding some super-team of caped crusading coders.
