Do you think there are certain settings that work better using certain editions? What I mean is this...
In 1E we had Greyhawk, and it seems to me that if I had to use strictly rules from one edition (not a hybrid), and if I were playing Greyhawk, I would definitely use 1E rules.
Same for the Forgotten Realms, because 1E had more flavor, more variety.
But when it comes to stuff like Dragonlance (yuck! ) and Planescape, for me I would probably need to use the 2E rules.
Lankhmar, 1E for sure. Ravenloft...hmmm. It's a hard call. Probably 2E?
I'm not sure why, but some settings to me seem to fit better in certain editions.
I suppose it's a matter of personal preference. Since Greyhawk was the original setting, it follows that 1E should be the most likely compatible and therefore used edition. With one or two exceptions, the 2E GH stuff by TSR was pretty forgettable. OTOH, since they (TSR) decided to make FR their default setting after 2E was released, it seems logical to me that that edition matches up well. I was turned off by DL because of the pathetic and incredibly poorly written novels I read. If ever there was a race deserving of genocide, it's kender. That said, DL is definitely 2E. Most of the other settings held no interest to me, although as the years have passed, I've discovered I kind of like some of the D&D basic settings, especially the Gazeteer series which I guess is Mystara? Most of which I've read ports to 1E very easily. What little I've read of Ravenloft I would definitely say is 2E. Same for Dark Sun & Planescape. Have read nothing of Eberron since it's their default 3E setting. I try to keep in mind that except for FR, GH and a little of DL, the rest of these settings came out after 2E was released and so were written with that edition in mind.
Sort of expanding on what Billy said, most settings have the rules of whatever edition they were created under baked into their lore, so they tend to fit better for that particular edition. Eberron works best with 3E, Planescape works best for 2E, and so forth.
As an example, when Dragonlance was released under 1E, part of the lore was that there was an international guild of wizards, and one of the rules of that guild was that mages could only use daggers and staves as weapons. This was fine, because it synced up with the way magic users worked under 1E. Later editions opened up the options of weapon use for mages, but the lore stayed the same. So newcomers to Dragonlance would get confused by this. "Why can't my wizard use a sword in DL? He can in GH and FR." Another issue is the word 'sorcerer.' The international guild I mentioned is called the High Wizards of Sorcery. Back in 1E, 'sorcerer' and 'wizard' were basically interchangeable terms. But 3E introduced a sorcerer class, which worked differently than the wizard class, and...well, it just caused a lot of confusion for newcomers, to be sure. Plus, Dragonlance treats magical items as rare, because they were back in 1E and even 2E, but by the time 3E rolled around, magical items could be created by low level characters and this fact did not fit the lore at all. (Ironically, magical items are rare again in 5E, so it fits again.)
This is also why the older settings tend to have a lot of 'cataclysms' as they are updated to new editions, so that the lore can be hammered into place to fit the new edition's mechanics. For instance, Forgotten Realms has the Time of Troubles to explain the shift to 2E, and the Spellplague to explain the shift to 4E. Dragonlance has the Chaos War for the shift to SAGA and the War of Souls for the shift to 3E. Which means for some of these settings, which edition 'fits best' kind of depends on the era you are playing in. For instance, it would be difficult to run a 1E Dragonlance game that took place after the War of Souls. Or since Dragonlance was never updated to 5E, running a game with it at all can cause some difficulties. (Not saying it cannot be done, mind you; in fact, I'm in a 5E Dragonlance game right now; I'm just saying, it takes some work to make it fit).
Consequently, this is why I have to disagree that Dragonlance was made for 2E or fits better with it. As someone who has run multiple 2E Dragonlance games, I can assure you this isn't so. Second Edition did not even exist yet when Dragonlance was first released (1984), and it shows in the mechanics. Whenever someone wants to play a bard, for instance, things get tricky. Because 2E style bards do not fit the lore of the setting at all. On the other hand, 1E style bards would work just fine. (It also doesn't help that the official 2E rules for Dragonlance are a byzantine hot mess, even by 2E standards. I usually wind up chucking them and just making my own.)
) and Planescape, for me I would probably need to use the 2E rules. 
