My first D&D experience happened sometime between 1977 and early 1981, but I don't know for sure when (I do happen to know, for largely esoteric reasons, that it was between the releases of Star Wars and The Empire Strikes Back--although probably closer to the later side of that range than the earlier.) The poor guy who wanted to get a very disinterested player (me) interested in this weird talky game that he wanted to run for me, but about which he clearly knew very little, did a poor job, and my experience with what was the original version of OD&D was not a positive or memorable one.
At some point in the next few years after that, I came into possession of The Official Advanced Dungeons & Dragons Coloring Album, which was a fascinating book altogether. Not only did it put the stereotypical Gygaxian dungeoncrawl into a semblance of prose (written by Gygax himself) but it included a mini-game in the middle that was my first real introduction to the concept of fantasy roleplaying. In addition, I stumbled across the works of Lloyd Alexander, then J. R. R. Tolkien (although only The Hobbit still at this phase) so I was finally ready to appreciate the potential of D&D when friends of mine started popping up at school with copies of the Moldvay Basic set and it's companion, the Cook Expert set.
Of course, the school year that I discovered this, I didn't actually play. I read the books. I marveled at the art. I conceptualized how I wanted the game to work. And after that school year, I got to play. But by that time, the people I knew who played did it with AD&D, so that's what I played too.
But I didn't particularly like AD&D. It didn't emulate the kinds of books that I liked reading. It was clearly designed and optimized for dungeoncrawling, and I found that paradigm more and more boring the more I looked at it... and I never liked it that much to start with.
So, sometime in the mid-80s or so, before AD&D 2e came out, I left D&D altogether for greener pastures. I kept checking books out here and there, flipping through them at the bookstore and whatnot, but I didn't play it. In fact, I got busy enough with other things that I didn't play anything at all.
Several years later, in the mid-90s, I stumbled across the White Wolf model of roleplaying games, and in my naivete, I thought that's exactly what I wanted RPGs to be. My affair with them was relatively brief, but then again, my exposure to D&D, while prolonged, wasn't really based on tons and tons of actual playtime either. Heck, I almost played more Top Secret or Star Frontiers than I did D&D back in the day. I lost interest in the Storyteller games, but not before picking up tons of Werewolf: The Apocalypse splatbooks and hanging around on the incipient internet on Usenet groups and list-serves devoted to that game. While I now look back at my White Wolf phase and kind of laugh at myself, it did accomplish something of note: it got me very interested in roleplaying again at a time when my interest in it had waned considerably.
At about that same time, I stumbled across a friend's apartment (I think I was picking him up and we were going to go do something, but I can't remember for sure) and saw that he had a copy of TSR's Top Secret S.I. I simulataneously found that another friend was also an old-time roleplayer, with an especial interest in the game Traveller. With me as the glue between us, I got these two guys together, we roped in the first friend's room-mate, and we had the first real roleplaying experience I'd had in quite some time playing spies using a fairly hand-waved interpretation of the Top Secret rules. From that point on, I've listed RPGs as one of my top hobbies continuously.
In 2000, I'd finally finished grad school and was working for real, making some real money, and actually had more free time than I had in the few years prior. Poking around on the internet at RPG discussion venues, such as rpg.net, I discovered that D&D was on the verge of releasing a brand new edition, and that it would be substantially revamped. Despite the fact that the tagline of that era was "Back to the dungeon" I convinced myself that D&D was going to be "modernized" to the extent that I could possibly enjoy it, and that largely ended up being true. Despite the "back to the dungeon" mentality, the designers wisely choose to make 3e an edition that easily supported lots of different playstyles and tastes.
While I still had to struggle for some time to overcome my distaste for lots of lingering "D&Disms", I mostly and eventually embraced this edition, and with the use of some judicious houserules (many of which were published by Wizards of the Coast themselves in the brilliant book Unearthed Arcana) I've made it into what is possibly the "last system" I'll ever play. Maybe.
Of course, that's not quite the whole story. After more or less happily settling into a 3e groove, after just a few years, WotC released 3.5 which I saw as completely unnecessary and a transparent and unwelcome money grab. It turns out that was exactly what it was: Rick Marshall's recent posts at Grognardia, which I linked to earlier, show that nobody at WotC thought releasing that was either necessary or even a good idea, but unexpectedly the management at Hasbro beat WotC into shape in the pursuit of short-term higher profits rather than long-term industry health.
Despite the fact that I was cynically disillusioned and not at all excited about the release of 3.5, I eventually made my peace with it and even came to embrace it. There are a few reasons for this:
1) Backwards compatibility with 3e was very high. If you wanted to, you could (almost) play with intermixed rules with no one being the wiser. As it was, you mostly only had to worry about the skill consolidations when converting, and that was simple and easy to do in your head; everything else could be intermixed.
2) The SRD was (and still is) online for free. To this day, the only 3.5 core book that I bought is the Monster Manual and that's just because I like monsters a lot and that's one book where the improvements were significant enough that I really appreciate them. If I need the udpated class or race rules (I don't think much changed with the races) or updates spell descriptions, I can get it online for free.
3) Although it was a close thing, I think that 3.5 was mostly an improvement on 3e. This was epsecially apparent in the books beyond the core books, though. Comparing, for example, 3e's Sword & Fist splatbook on combat melee classes with 3.5's Complete Warrior is night and day. And Complete Warrior was probably the most primitive of the 3.5 splatbooks; they only got even better from there. The Expanded Psionic's Handbook was light-years better than the original Psionic Handbook; in every regard, the splatbooks got better. And even with the core books, the designer's made an obvious effort to bulk them up with new content and not expect us to be happy to shell out $90 for just a slightly tweaked rule-system.
4) Yeah, 3.5 really started releasing a lot more sourcebooks than 3e had done, but by and large they were pretty good sourcebooks that I've enjoyed having. I thought the monster focus sourcebooks were a great idea, and mostly were well implemented. I thought the environmental focus sourcebooks were a great idea and ... well, somewhat mediocre execution on those, but they're still worth having for the most part. It had the phenomenal toolkit Unearthed Arcana which may be the best D&D book ever released (in spite of its extremely dry text, I get more use out of this book than any other, besides the Player's Handbook of course.) It also had the phenomenal setting search process, which is about the best community and buy-in project I've ever seen in RPGiana. And while many people weren't necessarily thrilled with the new setting that it generated (Eberron) I am. In fact, I think it's one of the best official D&D settings we've had, if not the best.
Of course, the 3.5 lifecycle had it's ups and downs too. After the publication of Player's Handbook II, the game seemed to take on a vibe of escalation. From that point on, stuff had to be better than what preceded it (during the Complete series, they almost went the other direction; I think a lot of the Complete classes needed a bit of a boost to be equivalent to their PHB counterparts, for example.) They got more experimental, and while some ideas were pretty cool and very different from what D&D of any edition had shown us before (like the Binder class, for example, and a lot of the stuff in Monster Manual V) a lot of it was hit or miss and even the good ideas weren't necessarily implemented very well. I actually don't use much of the late stage 3.5 material at all, but I do consider the Complete series to be as "core" to me as the actual core books.
Interestingly enough, the change from 3e to 3.5 was largely paralleled by the development of the Pathfinder RPG. While, arguably, there wasn't any need to make changes at all to the game, Jason Buhlman and the rest of the Paizo crew decided that if they were going to re-release D&D 3.5 under a new title, they might as well put their stamp on it and clean up a lot of what had gone before. It had, at this point, actually been long enough since 3.5 was released that there wasn't nearly as much outrage amongst gamers generally; and in fact, Pathfinder generated a lot of goodwill by being the spiritual successor to 3.5 in an era when outrage was more focused on the impending release of 4e instead. And I think a lot of people were more open to the idea that 3.5 had a few creaky seams that needed to be patched up. And the open playtest, where two different Beta versions of the rules were released for free and Paizo solicited as much feedback as they could on them, really generated a lot of community goodwill too.
But for me personally, I thought the change had the same impact as 3.5. It wasn't necessary. And arguably, Pathfinder has more compatability issues with 3.5 than 3.5 had with 3e. If nothing else, the implicit power levels of the basic classes and races are not the same, meaning that they can't be freely mixed and matched. Other elements mesh together with less drama, and some changes are even quite welcome (further consolidation and rationalization of the skill list, for example) but although I eventually made my peace with 3.5 and embraced the change, I don't see that happening anytime soon with Paizo and Pathfinder. Rather, I've cherry-picked a handful of houserules where I think they did stuff better (skill consolidation and special combat maneuver consilidation, in particular--I also cherry-picked a few rules from the Trailblazer document which, like Pathfinder, was an attempt to patch a few holes in 3.5.)
Why am I rambling on with this retrospective? I dunno. I think it's useful to sometimes examine what you're doing and make sure that the reasons you're doing it haven't become obsolete. I still like D&D. I still like 3.5. I'm still playing it, and probably will be for quite some time (because we're only 1/3 of the way through the Rise of the Runelords adventure path and our play frequency isn't all that great. It may take us nearly to Easter to get 1/2 of the way through. And let's face it; when we're done, we'll probably start another 3.5 campaign anyway.) I still am not interesting in branching out to new systems. I've made my peace with the problems I had with 3.5, and I'm still happy with my solutions.
My personal "State of the Hobby" address concludes that all is well.