TBH, I never did Icecrown dailies or tourney dailies, I think youre gonna hate the grind. I'd just jump right in, get a dedicated healer, buy a few items for her, and buy a few tank items (stam stam stam), Im not saying spend 20k, but around 3-4 for healer and tank. Then run random normals, get the 2 badges, and gear up like that. Soon youll find that you can do random heroic, and pick and choose instances if the one given to you is too hard. This is the fastest way and probably the most fun.