i vote for 44/16. i do most of my ridin' in boston and i live atop a pretty good hill. i haven't found a hill yet i had to get off or switchback up. and on the flats, rollin' 44/16 is great for me. dependin' on where ya are, try that.

edit--i see you're in florida! dude, bang a bigger gear. i think the highest point in florida is only about a hundred feet. go big!