I just had to buy a new laptop, as mine crashed bigtime. Debated between HP and going Mac. Well, I feel like a bit of a sellout, but I went Mac. Tired of all the quality issues with PCs. And a friend from high school, who works in computers, recently bought a macbook and said he would never spend the money on a PC laptop again, even if they are cheaper. And actually, between the 2 laptops I was comparing, the Macbook Pro 13" was only slightly more expensive for about the same specs. (took the education discount).
As far as residency, the match, and reputation... when I was on the interview trail, I heard many good comments about our clinical training at MCW. Apparently we do true sub-i's, while at some schools it sounds like their responsibility is less. A lot of the match process is individual - where your personal preferences lie in where you end up and what kind of work you put into your grades/Step 1. I interviewed all over the country including Columbia, Duke, UCSF, UCLA, Wash U, Northwestern, U of Chicago, Mayo. I never got the impression that my attending MCW was anything but a plus.
The financial aid budget is tight. I did not have a roommate and had to supplement with credit card usage - bad idea, btw. With a roommate, it's not so bad, but not much give either.
I highly recommend doing any activities during orientation week, or pre-orientation week. I met awesome people during pre-orientation who became good friends. Socially, you may become behind the ball without attending these things. May sound dumb, but it's true. With the class size similar to high school, rather than college, people tend to group up rather quickly. Plus the stuff was fun!
I gotta go to bed now - rest up for my not-so-easy internship. Hope some of that helped!
That and I'm doing anesthesia? 
