[If I Ran the Circus] Operation Back Hall Closet

Since you asked (Didn't you? I could have sworn you did)...
... if I were D&D's product manager, my goal would be to put an entry-level D&D boxed set in every back hall closet in America, sandwiched between the ubiquitous dogeared copies of Risk, Scrabble, and Monopoly. Let's stop trying to make D&D cool. D&D will never be cool, no matter how many tattooed elves we include or how many WoW-isms we slap on it. Hell, WoW isn't even remotely cool anymore. We need to distinguish cool from classic. Cool is ephemeral. Classic is forever.
I'm not talking about reprinting Homes or Moldvay word for word, but dammit, just make an evergreen edition of the game that combines the charm of Holmes and the scalability of Moldvay and be done with it. And sell it at Target next to Stratego and Life and Sorry!, dice and a few plastic minis included. Emphasize family play, with mom or dad as the DM, and kids as the players. Trade on older players' love for the game -- "the classic adventure game you loved as a kid is back, and it's easier to play than ever!" Have the boxed set include several short, thematically linked adventures that can be played in one or two sittings each.
Additional boxed sets would be self-contained adventures or campaigns, with relevant plastic minis and dungeon tiles. If you wanted to slap the D&D brand name on some new-school product, like WotC's recent slew of D&D-based boardgames, go ahead, but D&D the classic game would remain its own thing, apart from the D&D brand.
I've seen WotC groping at this idea, with the retro red box set, but there's a difference between retro and classic. It won't work until they stop trying to please the hardcore gamers (because there's no pleasing them ever) and go after a mass audience of lapsed gamers in their 30s and 40s who want to share a classic pastime with their kids.