I've tried to get into DF twice.
But the wiki, documentation, and videos are woefully insufficient to overcome the burden of trail and error.
Dont get me wrong, I like adversity, I like having shit blow up in my face at the beginning of games cause I'm a newb. That's what drives me forward in very complex games (xcom on insane, for example).
But with DF, its not the challange, or skill level, or even any kind of game-skill learning curve, its the retarded clunky fucking UI that's the problem. Keep the ASCII graphics, ok, sure. But revise the fucking menu system, cause it seems like a VCR manual writer came up with the damn menu system...and Ill be damned if ANYONE has laid out a good menu map for DF yet.
Nerds just can't write/communicate well. Sadly, that's the only beast that has mastered this heavily tarnished (read: unpolished) game.