The next phase of my involvement with D&D came decades later, barring a terrible AD&D campaign a friend of mine ran in college that I only participated in for a month or two, around the year 2000 when I started playing a heavily-house-ruled version of AD&D after I move to Pennsylvania, with a friend who’d been playing that same homebrew campaign-world since she was in high-school. She was one of those DMs who did all the rolling, and the the players were never sure what the rules actually were beyond what was on the character sheet. While I really loved getting together with these friends every week, I was actually kind of relieved on the weeks when we played board-games instead. The almost exclusive emphasis on dungeon crawling through fun-house dungeons, with turn-by-turn foot-by-foot mapping and minimal interaction between characters was pretty much everything I disliked in D&D. Eventually I learned to find the fun in it, mostly by trying to make each character memorable and distinct despite having basically no customization other than choosing a class (even race was restricted by a random roll for place of origin). Once her kids had all gone off to college we played D&D very rarely, though we still got together every Friday until the pandemic hit.
When Dungeons and Dragons 3rd edition was released, originally, I wasn’t much interested. I felt I had moved on from D&D, and a lot of what I liked in RPGs I viewed as being in opposition to the design of D&D. Eventually, though I picked up a copy just to see what everybody was talking about, and while I wasn’t smitten with it, it did seem to be a significantly more “modern” design as far as character customization and detailed resolution went. I wasn’t going to immediately switch my home group over to it, but around 2005 I was open to running it online for some friends who were interested in trying it and were having trouble finding local gamers.
This was in the long, long ago before there was anything like Roll 20 or Fantasy Grounds, but I found a (now discontinued) program called ScreenMonkey from NBos that promised to be at least a step up from playing purely over AIM or irc, and we gave it a whirl. That campaign actually lasted almost three years, and was set in the Forgotten Realms. Eventually what made me tire of it was exactly that… I really didn’t know or care much about Forgotten Realms, but some players were very into it, which is why they’d asked for an FR campaign in the first place. There wasn’t any blow up, but the mismatch between the effort it took to provide them with what they were looking for each week and how much I enjoyed running FR-based materials created entirely from scratch caused me to put it on hiatus that became permanent.
Meanwhile at some point my home group *did* switch over to playing 3e, at least as one of the games in our rotation, mostly because my friend Russell liked it and my group really liked his GMing and the setting he’d created. We had some really fun and memorable adventures, but I eventually noticed that the crunch was a real drag on the players as they leveled up. It got to the point where when they reached a new level, they just handed their character sheets over to Doug, our rules monkey, to do all the grunt work leveling them up. When Russell’s job stopped being bi-coastal, the once a month game turned into once-in-a-blue-moon, and that was pretty much it for our 3e experience.