[Using a broad definition of D&D to include all editions, retro-clones, etc.]
I started with the blue dragon, had the white box LBB, but really grew up on AD&D Efreeti and Gem Eyes. Played some in highschool and college. Then 2ed splat mania + too many crap products + (in retrospect) the shift in style, structure, and substance of those products as compared to 1ed era drove me from D&D (into other RPGs).
I returned to D&D a little after 3.5 release. I've since run and played enough of OD&D(Swords & Wizardry), Basic(Labyrinth Lord), AD&D(OSRIC), 3.5, and 4ed to arrive at the following opinion.
AD&D including (and even more so) 2ed is my least favorite edition of D&D to run/play. This was news to me as it's the edition I've played and run the most. The DMG is still a good resource and many of the classic modules I'll try to weave into campaigns. But, I won't be using AD&D rules to run them.
AD&D and it's clones are just so horribly fiddly, filled with wildly inconsistent levels of simulation and detail. Baroque were simple would suffice, vague or abstract were a little more is needed. Too many "broken" classes, combos and rules. It's the shored up, chronically patched half-way house between the wild and loose "earlier" systems and the mechanistic edifices to game theory of later editions.
There's a reason we have sayings along the lines of "right tool for the right job", "do one thing and do it well", "don't try to be all things to all people". It's cause of people like me.
I enjoy the ends of the spectrum. Where games, successful or not at getting there, at least know what they want to be. Sometimes I crave a fine dark chocolate. Sometimes an oily, 100% natural nut butter, the type that requires stirring. But, my desire for a waxy chocolate covered peanut like fudge thing is quite low.
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