Wow. I'm uncertain what to think of this, now. $10/month for Dragon and Dungeon together isn't so bad. As I've said elsewhere, I'd prefer my periodical content online, anyway. For Dungeon, I tend to heavily modify things like place names, deities, etc. and swap out some monsters or treasure. A cut/paste job from a PDF or web page saves me the time of retyping chunks of the module. Likewise, I tend to pick and choose from Dragon and PDFs are pretty easy to file in an order that makes a lot of sense to me.
Considering the amount of content I've historically used from Dragon and Dungeon, $10 is pushing my limit, but it sounds like the chargen and map/campaign tools are included, so that's all good.
Paying an extra buck or two per book to get it in an ultra-portable and cross-indexed format is worth it, too. Not to mention the boon if that price includes the chargen datasets, too.
If the quality stays high, I would expect that about $15/month for the whole shebang would be my limit. I've averaged about a book a month, plus Dungeon. If I move to a book every other month or less (likely anyway, because I'm tired of the rules glut -- maybe I'll move to only the PHBx, DMGx and Eberron books), the cost to me won't really change. I like that, especially since it sounds like the value (to me) would.
While I do have a few gamer friends who live in remote areas, my local group is currently full and takes up all my hobby time. So, I'm not a likely consumer of the VTT. If I were, though, I'd be outraged at the idea that someone would expect me to pay for random pixels. I can appreciate a premium cost associated with using the expanded minis sets and the work that goes into them. I just don't see any reason to keep the random aspect.
Still, I hope digicrack works for them. That would keep them in business and subsidize the portions of DDI that I will probably use.