The situation isn't helped when even WotC doesn't know how to market the line. What is "Dungeons & Dragons" today? Is it the three core books? Is it D&D Essentials? If the Starter Set is intended for people who have never played before, why use the nostalgia factor of the Mentzer Red Box artwork and trade dress?
Beyond these questions, on the actual subject of playing, The Chatty DM recently wrote about a D&D Essentials game that he ran for a group of media professionals working on geek-related TV shows and/or websites (part 1, part 2). Most of them were new to tabletop gaming. It turned out to be one of his best D&D games due to the energy level of the players, his design decisions, and some ideas that he incorporated into the game (one idea from Burning Wheel). It isn't necessarily about the mechanics, it's about play style and having fun.