To answer the original question, since some of this musicry is too over my head to be able to form a reasonable response: I actually just recently made this transition. A freind of mine who i carpooled with for about six months listens predominately to hardcore and metal, and over time he managed to get me into those genres by slowly easing me from the lighter, more melodically driven stuff i liked or could stand to some of his more ridiculous favorites.
I remember at the beginning he was playing for me things like Against Me!, Bear vs shark, and Black Flag. Every once in a while he'd play something by Dillinger Escape Plan or Converge just to mess with me. Then he discovered i liked Explosions In The Sky, so he showed me Pelican and Isis. At some point, i suddenly took a liking to Minor Threat, and he spent a lil while showing me various 80's hardcore and 90's power violence bands. Some elapsed time later, an i'm liking The Locust and An Albatross. Even more elapsed time later, i went to my first Converge concert. Was teh GVIM. Most fun part is avoiding the madmen(& women) running around flinging their arms about wildly. They gotta keep the crowd in line.
Zo, if that helps. Right now my tastes are largely in the realm of post-rock, with an appreciation for pop(indie or otherwise) and hardcore/metal.
Short of having a freind with opposing musical tastes to spend a lot of time with, i'd just download like mad. Give everything a listen. Keep stuff you hate in your library, so you can check back later. Or make fun of it.
I recently discovered A Tribe Called Quest. That may help you with th hip-hop. Thas about as far as i am into that realm.
I gunna havta check out some o you people's lists, though. Clearly i got a lot to learn. : P
Thaz it fer moi.