My $0.02...
1) my impression is you haven't really considered what risks you're taking on with riding, mostly because you don't seem interested in taking steps to mitigate that risk. (Also, riding in flipflops is a terrible idea, if you were planning on emulating that). I highly recommend you take some time to think about the bad things that can happen while riding, and how much of that risk you're willing to take on. Flip through a book like Proficient Motorcycling (
http://www.amazon.com/Proficient-Motorcycling-Ultimate-Guide-Riding/dp/1889540536). Not saying you shouldn't ride, but think beyond the fun and the image, and count the real risks you're going to take on by doing this.
2) listen to what people are telling you here about gear. Don't get leathers (especially not from Doc's) just because of the look. Get stuff that will (A) protect you when you fall (assume you will fall), and (B) you're willing to wear in hot weather when you're stuck bumper to bumper in downtown Toronto. You want a chin bar on your helmet (most frequently the impact zone in falls), armor in your jacket, gloves that will protect your knuckles and palms, boots with hard toes and ankle coverings, etc.,. Assume that you may have to skid on asphalt for ~10 seconds in whatever you're wearing (or not wearing), and make your gear decision appropriately. What is they say..."dress for the slide, not for the ride"?
3) Look into the metric cruisers (Honda, Kawasaki, Yamaha), they often provide better bang for the buck. I knew I wanted to do the cruiser thing so I picked up a Vulcan 900 as my first bike last year. The Vulcan was a great starter bike, plenty of power to keep you interested, and really nimble/easy to handle for the size. I got some flack for starting on a 900cc but had no trouble handling it at all (but I'm a pretty big guy). The bike is pretty forgiving overall, the torque rolls up gently, throttle's not twitchy. I highly recommend you look into the Vulcan/Shadow/V-Star, but if you've got your eyes set on a Sportster, go nuts. You can always sell it down the line. (incidentally, I'm selling my Vulcan 900 now after upgrading)
4) I upgraded to a Harley Night Rod Special very recently after test riding one. IMHO, the V-Rod is the only Harley worth owning. Not sure how you'd afford it as a student, but if you like the the Iron, look into the Nighster or the Night Rod - both might treat you better long-term. I recently rode my Night Rod 800km at 120+km/h, and was pretty comfortable on it. Not sure I could have said the same on a Sportster.