I've got to step out for a while, so I'll be unable to respond to any comments here but a thought occurred to me this morning that I wanted to throw out there for discussion.
Two common complaints about old school gaming is that it lacks "story" and that there's little interest in character development beyond what occurs as a result of gaining XP. I've already, I think, argued that both these complaints are utterly mistaken and result from a misreading of old school games (not to mention a misremembering of the history of the hobby). The big difference between the old school and the contemporary one is that the old school assumes that "story" and character development are things that evolve organically through play rather than something one presumes before play. The old school also allows for the possibility that neither story nor development will evolve and isn't willing to find ways to ensure that either takes place through the imposition of game mechanics designed to do so.
Anyway, what I was thinking about is that what makes old school gaming so appealing for me is that notion that, if I create a 1st-level Fighter, whom I call Conan and say is a young Cimmerian warrior out to find his fortune in the world, I actually have to play D&D well -- not to mention get lucky -- in order to fully realize that character. That is, it's not a given that because I create this character with dreams of one day ruling his own kingdom that he will in fact one day rule his own kingdom. I don't sit down with the referee and agree that, yes, the campaign "theme" will be about Conan's rise from obscurity to his accession to the throne of Aquilonia. Rather, I, as the player, decide that that's what I want to do with my lowly 1st-level Fighter and then I play the game with that in mind, doing everything I can to make that "story" that I've chosen come alive through play, but with the understanding that an unlucky dice roll -- or the whims of other players -- might derail that story, even ending it forever.
My point is that one of the essential features of old school play is that there are no guarantees. I sometimes think the hobby has emphasized the roleplaying aspect of RPG to such an extent that it's forgotten what the G stands for. Old school gaming never forgets that games typically involve chance and the best gamers are those who can roll with the punches randomness throws at them and succeed in spite of them. To me, there's more fun to be had in the story of a would-be Conan who actually fails at his player's original intended "story arc" and then goes on to do something else as befits the circumstances than one whose story arc has a conclusion that's foreordained by mutual agreement with the referee at the campaign's start. If you know your 1st-level Fighter is destined to become King of Aquilonia and that the whole campaign is about the steps to achieving that destiny, why bother? I don't personally see any fun in that and I think one of the big dividing lines between the old and new schools lies here.
Anyway, this is a random, inchoate thought, so be gentle. And play nicely while I'm gone. It might be a while before I can wade back into discussing this.