Like Philatomy Jurament, here's my relationship with D&D, which is basically skipped 2e and 4e, didn't try 5e (yet).
1981-1988: Played AD&D (1e), occasionally DM'd Oriental Adventurers. Loved it. Couldn't get enough (couldn't afford it because I was a kid).
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1989: Played 2nd Edition at release. Didn't like it much, as I was playing a Half-Orc Assassin and both things were "banned". Stopped playing D&D.
1989-1996: Didn't play D&D. Ran Top Secret/SI, Boot Hill (1974 & 2nd Edition), RECON, and Star Wars (West End Games D6). Even tried GURPS.
1996-2002: Ran AD&D (1e) games again. Live campaign from 1996, email from 1998 onwards.
~2002: Converted both games to 3e (2 years after release). Bought a metric bleep ton of stuff. Started playing in a 3e game too.
2003: Converted both of my games to 3.5e at release, with some grumbling from players. Game I was playing in also converted.
2008-2013: Bought 4e PHB on launch day, went to launch event in Seattle and got it signed. Game I was a player in converted to 4e, but I didn't like it, and the game died when the DM moved. Kept running 3.5e. Got preview Pathfinder rules printed copy from a local gaming store and gave my copy to Wolfgang Baur. Bought Pathfinder PBH at launch, and lots of Pathfinder adventures; used Pathfinder adventures converted to 3.5e and stole some rules from it. Attended PaizoCon twice, which is the only times I played by "full" Pathfinder rules.
2014-Present: Running a live and email 3.5e game, though not often for personal reasons. Not buying anything due to lack of time/interest. Bought the 5e PHB and the initial adventure, haven't played it yet.
With TSR, I found myself not being in step with the style/focus/direction of the products in the 2e period (really, that started in the late 1e period, but I soldiered on for a while). Eventually, I quit buying the new D&D stuff, ran other games and editions, and stopped caring about what TSR was doing. When WotC released 3.0, I got interested and started buying (new) D&D stuff, again, and that held true up until shortly after 3.5, when I started finding myself out of step, once more. Took a look at 4e, but it was an even greater departure from my kind of D&D, so again, I'm back to "not buying the new D&D stuff, running other games and editions, and not paying attention to what WotC is doing."