With the reliance on rules that's been beaten into players and DM's since 3.x, and with the decline in reading in general along with the rise of the MMORPG, are we crippling future DM's?
I mean, even if we can get a DM to know and understand that the rules are advisory only, and he can do what he wants, is his background and experience in strict rules reliance going to be a hindrance to being able to freewheel it and go with his imagination? This hindrance would potentially apply to both adventure design, as well as to handling individual situations.
Not only that, but look at the environments OD&D came out of, as compared to today, historically speaking. D&D was created just after Woodstock and the hippies, where it was do you own thing, to hell with rules and authority, and "Screw the man!", where kids even in high school would blow off school to go protest stuff.
Kids today now have their lockers searched at the whim of the principal, and don't seem to give a shit. As opposed to just getting home from school and going outside and playing, using their imaginations and making up games with the neighborhood kids, they have "structured activities," from morning to night. Their lives are, to me, a structured nightmare. But its what they are used to. Hell, in my high school in the mid-80's, the kids had a smoking area outside we could go have a cigarette. Half of them smoked a joint, and the teachers knew, but never did anything about it.
The other problem is the BANE that is "Political Correctness," where certain behavior is frowned on by everyone under a certain age, because they feel they must, and not because of a personal belief. Even worse, for many, political correctness has actually become the personal belief system of what's right and wrong.
With all that going on, with all the "un-learning" that needs to happen with Gen-Y, GEn-Z or whatever they are up to now, it almost seems an uphill battle to get younger DM's who can really be good enough to get more people their age into the game and carry the hobby forward.