Okay, I'm familiar with most of these, so i'll give it a shot...
1. Reputation:
1) UPenn/Duke, with UPenn having a little more pull in the northeast
2) NYU/UChicago, with UChicago being maybe a bit better
3) Albert Einstein (though not far behind NYU)
2. Residency match:
Hands down, Duke and UPenn have the 'top' matches as far as students ending up in prestigious hospitals, though the other three certainly hold their own. I think that probably one of the biggest things to look at is that students tend to end up in more local hospitals for NYU, Einstein, and UChicago, while Duke's and UPenn's students are a bit more spread out. However, this also probably has more to do with preference than ability.
3. My Opinion.
Personally, I would chose UPenn first, then Duke, then NYU/UChicago, and then Einstein. I like UPenn's curruculum, and you can't beat their rep. Duke is beautiful, and I presonally like NC, but it's not for everyone. Also, doing all of the science courses in one year seems sort of overwhelming. NYU, in my opinion, is overrated, and despite popular opinion, crammed dorms in manhattan aren't the best living situation. I don't know much about UChicago, so I really can't comment. Einstein is a solid school, especially if you want to stay local or go into more of a primary care specialty or surgery. I didn't like their location, facilities, or Orthodox Jewish policies (library and gym closed friday evenings/Saturdays, etc).
4. Yeah, I think it's too rushed. But you should really ask a current Duke student about that.
5. UPenn - only 1.5 years of basic science (though Pitt has that too now! yay!), and some great clinical opportunities.
Good luck!
Quid