While not counting several other abortive setting design attempts that really never managed to be more than a one-page or so "high concept" idea, the many one-shots I ran where no setting was significantly developed, or the handful of non-homebrewed games that I ran in settings like Eberron or Iron Kingdoms or Golarion, most of my setting design efforts over the last ten or eleven years can be binned into one of four "streams." By this I mean that one setting evolved into another that was its direct successor. Of course, a number of elements became "areal features" that spread across streams freely, and one setting (by design) really didn't have a clear-cut successor because large chunks of it were migrated in toto into more than one successor setting. But, the streams are still easily recognizable.
Also keep in mind that through most of the last couple of years of the 80s and all of the 90s I was either not playing RPGs at all, or at least studiously avoiding D&D and playing other games instead. I dropped out of D&D before 2nd edition, because it was clear to me that while I could see a lot of fun potential inherent in the idea of fantasy roleplaying games, D&D specifically catered to a gaming experience that I wasn't very interested in. Ironically, 2nd edition would probably have been more up my alley at least in some ways, because I would have appreciated the wealth of unusual settings that came out at that time, but I would also have been increasingly frustrated by the system, which I never liked and which I grew to like less and less over time. Of course, I could have played with the Rules Cyclopedia, but honestly, I'm not sure that I really understood at the time the difference between D&D and AD&D; seeing them both as somewhat interchangeable. Even now, I don't think that the differences would have been enough to tempt me from one to the other; many of the elements that frustrated me the most were common to both systems anyway.
But after a few years of being more or less completely disconnected from the hobby, I got back into it in the mid-90s playing games like MegaTraveller and Top Secret S.I. (both of which were a few years old at the time.) Then I wandered into White Wolf territory, and while Vampire wasn't quite my speed, Werewolf: The Apocalypse was. I think I was initially excited by the premise of playing a game that focused less on the gamist and arbitrary elements that so frustrated me about my old D&D games and focusing on a Narrativist approach.
Of course, after a while, I came to see White Wolf as both pretentious and hypocritical; but that's beside the point. Needless to say, I wandered away from White Wolf, having learned a few lessons about what it is that I want from a gaming experience, and most especially, having re-embraced RPGs as a hobby. This was in early 2000. Just in time for me to be hanging around online messageboards and whatnot like rpg.net in time to hear all the buzz about the upcoming D&D 3e. And it occured to me that quite possibly fantasy was what I liked best after all if only I could find a system that was flexible enough to allow me to run the kinds of games I wanted without all kinds of weird arbitrariness, and without any support whatsoever in the mechanics if I wanted to "go off the rails" so to speak and ditch the whole tiresome dungeoneering experience. By happy coincidence, at about this same time, I finished grad school so my time and income were significantly "freed up"--I ended up buying a lot more D&D 3e products than I had of any other game system--in fact of all other game systems combined.
And for a while, I was headily embracing the 3e experience, by and large. Back in those days, Dragon Magazine was operated in-house by Wizards of the Coast still, and on the WotC website, there was a section for Dragon Magazine. This section had the full text of all the DungeonCraft column by Ray Winninger posted online, and I quickly read through this material, grabbed the text from these articles and saved it on my hard drive, and decided to use the process, which was a good match for my style anyway, to flex my atrophied fantasy homebrewing muscles a bit.
This first setting, which I worked on possibly as early as late 2000 but certainly by early 2001, didn't diverge much from the standard D&D implicit setting. In fact, because I was unused to working in the D&D milieu, I actually actively used the tools available to me rather than trying to think very far out of the box at this point. Plus, quite honestly, I think I was kind of impressed with the Dungeoncraft sample setting, Aris, and I subconsciously mimicked some aspects of it. Certainly that first setting was very much in the vein of traditional, Medieval fantasy with a D&D overlay.
It wasn't long before I started taking my development online, and that's when this early DungeonCraft setting started morphing into Faerytale. Not only was I now putting setting information up on GeoCities (ah, I miss them) but I was making a more active attempt to tie setting elements and rules together, coming up with sensible ways in which races like elves and dwarves interacted with the setting, and notably I turned away from the bright and polite Medievalist fantasy approach. See, I've long been a fan of all kinds of adventure stories, not just fantasy. I've been a huge fan of swashbuckling romances as long as I can remember (Errol Flynn was my first favorite movie star when I was a kid, and I spent hour after hour up in the branches of the trees in our yard pretending like they were the masts and rigging of a pirate ship.) I'd long liked cowboys and indians drama. Flash Gordon and John Carter and Tarzan were amongst my favorite literary characters. I'd read spy thrillers like The Holcroft Covenant, The Matarese Circle, or The Bourne Identity by Robert Ludlum. I was a fan of the conspiracy theory stylings of The X-files. And I was gradually starting to think to myself how I could incorporate elements of all these other adventure stories that I liked. So in Faerytale, the assumption was that the PCs would be agents of the government; a special task force, if you will, sent to deal with supernatural threats. Threats that most people didn't actually believe in, but which were true nonetheless. This very overt X-filesism and it's theme of near horror became an important point for me, as it continued on down to most of the settings that I've since worked with.
I never ran either the first DungeonCraft setting, nor Faerytale, yet I started to feel like I was migrating even further away from the D&D conceits after a time. Late in 2000, Wizards of the Coast released the d20 Star Wars game, and followed that up in 2001 with d20 games like The Wheel of Time and Call of Cthulhu, finally concluding their efforts to create all new d20 games with d20 Modern in 2002. This was when I first started entertaining more radical redesigns of the rules to better accomplish what I want from the game. Faerytale II went live sometime around then, utilizing a number of houserules, including alt.classes from the Wheel of Time game and alt.races, many of which I tweaked myself. And that was the tipping point; where my break with D&D really started, way back in the very early days of 3e, before 3.5 came out. From that moment on, I never really ran D&D "as written" except under duress. And that's the most lasting legacy of this first stream of homebrews; the tone, the theme, and the willingness to mangle the rules to get them to do what I wanted them to.