All the talk about supporting all the past versions of D&D (or rather, the players from past versions) has brought up, in many forums, blogs and tweets, the discussion about the actual gameplay, the flow of the game.
To recap, in the early days, it was all about imagination, storytelling, and dialogue between the DM and the players. The DM told a story, but allowed the players to steer that story, and it was all a back-and-forth collaboration. The game was about orally telling an epic tale around the dining room table, instead of around a fire like the players' ancestors did. The DM was the ultimate rule of law in how the story went, though, and could nix attempts that the players made to steer it away from his or her overall plans, if necessary. And, once in a while, the DM might have the players roll some dice to add some mystery and chance into the mix.
As versions progressed, and players become more seasoned, the Player's Rights seemed to spring into being, where they had a right to dictate how to story went, even if against the DM's wishes. The checks-and-balances, then, became the ruleset and a more frequent use of the dice: if the player wanted to slay the dragon, the DM didn't have to argue with them that "no, you're level 3 fighter really has no chance of taking on that elder wyrm, no matter how brave, valiant, honourable and lucky his is"; he could just cede to the roll of the dice, knowing full well that there was no way that the player would pull that off (or, if the rules allowed critical hits and vorpal weapon rolls and the like, then the DM would accept that this was indeed an epic turn to his or her adventure.)
And then the game progressed further, and players evolved further, and came from another realm, a world where the story was "told" by machines (the world of computer RPGs), and thus their training was steeped in the art of Min/Maxing, and the game designers had to accommodate for this: they had to protect the poor DM from the unbalancing problem of every fighter taking weapon X and every wizard taking spell Y, and so the fool's errand of balancing the game was introduced, and along with more rules to aid in this balancing, the game became more number-oriented, more dice-oriented, and less imaginative - it became more of a wargame than a storytelling game, from the player's point-of-view anyway.
And now... they want to be able to support all of these players?
As a DM, since 3rd edition, I've always tried (and I stress the "try" part) to be a DM somewhere in the middle - a DM that allows the players to come up with solutions that aren't listed in their Skill list or Feat list, or covered in a table in the Player's Handbook or DM's Guide. I do, however, try to quickly find a way to make the request relevant to the representation of the character on the character sheet - that is, to find a way to use an ability score, or skill check, to give the player that way of "attempting" their idea with their dice and some modifier.
Sometimes, if I think that there should be no way of failing, I'll ask the player what their score in such-and-such ability is, and make a show of nodding and thoughtfully, deciding that yes, that's an adequately high-enough score to succeed at what they're trying, or that yes, that number of ranks along with their racial bonus makes that obscure skill-like idea possible. Other times, I'll ask them to roll, completely planning on telling them succeed regardless of the outcome (just to give them that worry that they might fail, and their best-laid plans are going to cause more trouble than they're already in), only to have to scramble when they roll a 1 -- I can't fess up at that point that I really wanted them to succeed all along, can I? So quick-thinking is required to have them actually fail, but for that failure to not be as bad as it should be.
But sometimes the math is good to have. Sometimes I'm not sure how easily this rag-tag group of characters should be able to dispatch this group of monsters, especially if they foolishly raced ahead after the last battle without so much as a healing spell from the cleric. In the old, storytelling days, the DM might "punish" the party for their foolhardiness by having one or two party members severely wounded (and then allowing a retreat if the party smartens up); but perhaps allowing the party to advance and persevere with a non-stop onslaught against the enemy is worthy of some future bard's song. Myself, I'd rather let the (somewhat) balanced numbers -- and the wildly karma-affected rolls of the dice -- make that decision for me.
But I will admit (but never to my players' faces), that sometimes I will fudge the numbers (more on my side of the DM screen than their own) if I think the dice are to blame, and not the players, for what would otherwise be a dismal outcome. If the players should have rightfully been able to defeat a simple group of guards, but the paladin's dice were completely against her, I'm not opposed to "cheating" -- and that *is* how some people see it, that "the rules say..."
Sticking to the numbers can be good! It's a way of keeping the campaign's story somewhat realistic (perhaps ironically, for a fantasy game), ensuring that incredible feats are possible (as they should be, because the players are all heroes), but also keeping a rein on something too fantastic, too out there, that the story becomes uninteresting to the players and to any third-party observers that might hear or read about it.
Because while my players will possibly disagree, given the sheer number of Total Party Kills they've had over the years, for me it *is* still about the story. It should be the source of tales around future dining room tables, and should be believable -- fantastically believable -- and not stories of Monty Hauls and DMs that are pandering to their players with vorpal weapons just to keep them playing.