I never played Dungeons and Dragons as a kid (born in the early 80s, so a bit too young) but I played a lot of Games Workshop games (Warhammer etc) and I played D&D-based video games (Baldur's Gate etc) heavily.
I remember poring over rulebooks and probability tables for hours, and writing computer simulations (in Visual Basic or Excel) to try and find some edge in the game. I think my parents were pretty worried about me.
I now write stock market simulations and come up with trading strategies for a living, using essentially the same methods that I used in the mid 1990s to win at roleplaying games, so I guess it all worked out okay?