Good question... I'm getting pretty decent at the hill in Prospect Park too, but am worrying about anything steeper. I have a triple, but am considering a 26t chainring to replace the 30t chainring to give myself a couple of even easier gears than I have already. There just really aren't any steep enough hills in Brooklyn to practice on! What about using a trainer? How can you simulate a hill on a trainer? Must be a decent way...