What would you do differently about your first year having gone through the experience?
And I know we keep going over living arrangements over and over, but for anyone still willing to answer:
Where did you chose to live and why? Would you make the same living arrangements again if you could do it all over?
I'll take a stab at it. Regarding first year, as a current first year, I'm not sure that I really would do anything differently. The curriculum in the first quarter will be dramatically different, schedule-wise, for the incoming class than what we had, so commenting on the first quarter is more or less pointless. Nevertheless, I'm not one to go to class and I wouldn't change that. I think I've been learning the material just as well and have been doing just as well on the exams as my classmates, while freeing up a lot of free time. I've never felt as if I don't have enough time on my hands. Make it a point to continue the things you enjoy, be it reading, exercising, whatever. You do have the time, whatever you might think.
Regarding living arrangements, I chose to live by myself in a studio situated at 53rd & Dorchester, and have no regrets. It's very affordable ($750/mo with utilities and gym included), plenty of space, private and secure--and, most importantly, right where all the affordable food is (two Chinese places, Ribs 'n' Bibs, Subway, Nathan's Jamaican, Hyde Park Gyros, Boston Market, Dunkin' Donuts & Dunkin' Deli open 24/7, and some veggie sub place all within a single block, and many more when you expand it to two blocks). I eat out essentially every meal and have no issues with money, because each of those places is very affordable. Other conveniences are right around there, as well. It's a safe and easy 18 minute walk door-to-door with the medical school, less than that to the #6 express bus that goes downtown, three blocks from the Metra that also goes downtown, a block from Bank of America and WaMu... all in all, I feel as if I have the ideal location in Hyde Park. I wanted to live by myself first year because I didn't know anyone, and I carry very strange sleep/wake hours that might be annoying to anyone I may have lived with.
Would I do it again? Absolutely. I don't have a car and can't think of a better place to live for the price, convenience and comfort. That said, I'm still considering a move downtown for the second year just for kicks.
Really, in terms of safety (this is my humble perspective), you should be perfectly fine between 47th and 59th Streets north to south, and between Cottage Grove and the lake west to east. If you're curious about a specific location, I'll be happy to offer my opinion if I'm familiar with it, but that's my rule of thumb.