I would play 2ed. under just about any circumstances or any setting. Home Grown, Grey Hawk, Al Qadim, Ravenloft, Darksun, Forgotten Realms, heck even Hollow World you name it. 2ed. just seemed to have all of the diversity that you would look for in a game that published verious different settings as well various different types of settings.
Truthfully, I think 3ed in a lot of ways ruined not only D&D but a slew of other games as well. I don't think that Wizards of the coast in all of their "GAME DESIGNING GENIUS" (don't worry, I'm not about to go off on another rant of 'comedic opinion'...I remember how well the last one went over.) quite realized exactly what they were doing when they decided to have an open gaming license for D20. I mean sure now it's easier to min-max a character or two, but that sort of looses it's charm after the second Dwarf-Wizard-Spellfire Weilder-Theif-Kensei that you make.
And yes you'd need to be playing under a good DM/GM/Story-Teller/Referee/Zombie Master/Zartan('ya know if you ever feel like busting out with the old Hero Quest Game), but even with a good DM... 3ed in its entirety still allows for Cybernetically enhanced, Red Talon/Brujah abination, Jedi Guardian, Panzerhand wearing, gun weilding Kensei, half dragon, super spy ninjas who can drive Steam Jacks...(yeah I tried to fit in more ananlogies but it's late).
I guess what I'm trying to say is that...all I really want for christmas is for Wizards of the Coast to dissapear of of the face of the Earth so that maybe in a generation or two their "Buy more books-Get better Characters" mentallity will vanish from the minds of all gamers, and with thier inexplicable dissapearance, everything they've ever printed might be worth something someday
GYGAX FOR PRESIDENT '08!!!