As none of my CAD programs perform that function for me I just pick off similar looking areas from the plan, get their area and slope, and do a composite slope (i.e. pro-rate the areas). I don't get too wound up in perfection but I try to be as diligent as possible with it.
There's a whole host of methods for figuring Tc. I see a lot of people using the SCS method, and I used to use that one quite a bit, but now I generally use the lag/CN method.
I think as long as you're consistent and use sound judgement then it's use whatever you're most comfortable with. Though I suppose you don't want to use the FAA method on a hilly, woodsy site ;-)