Today's #RPGaDay2016 prompt is: most challenging but rewarding system you've learned.
By far the most complex system I've played regularly is D&D 3-3.5. The amount of feats, prestige classes, and subsystems for things like grappling just sent my head spinning. And since it was my first proper experience with roleplaying, I tried to learn it all so I could "play it right".
While I no longer think it's a system I'd want to run again (and Pathfinder doesn't really appeal either), I'm -glad- that there was so much complexity. It gave something interesting to engage in, and the promise of the same sort of strategic depth that Magic: the Gathering had. I'm not sure I would have stayed interested in roleplaying if not for that perceived depth. You can probably tell by my hedging language that I no longer believe this. I think the rules were bloated and the depth illusory, especially once you got into the OGL d20 third-party supplements. The enormous success of 3rd ed and the OGL spawned an incredible ecosystem of games.
Once I had a grasp of d20, there was this whole wide world of other settings and games built on it, and through them I discovered the enormous variety in tabletop gaming. The separation of system and setting really intrigued me, and I think some of the design decisions I like in games is related to that, as is an enduring interest in generic game systems. Expanding beyond D&D was possible because I could try running d20 Modern and Mutants and Masterminds--a trail of breadcrumbs leading to different types of games.
I also don't think I would be as interested in story games and rules-lite systems if I wasn't responding to the crunchiness of 3.5 (and later, 4e). I wouldn't have as broad an interest in roleplaying games either. And I might not even have kept roleplaying in the first place! So thanks, 3rd ed, for being a useful stepping stone.
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