Not original OP here, but the OP who re-sparked this conversation after getting admitted and offered the Ruby last week.
I did just return from Chicago. It's a freezing cold city, but also a beautiful and interesting one. And it's way cleaner than New York and SF. (New York smells so horrible). The University of Chicago's law school is really ugly, as a side note. And tiny. And a bit low on amentities.
There's pretty solid support for Ruby's, sorta to the point that makes me feel uncomfortable about how they're treated vs. the rest of UChi. If you look at clerkships, Rubies account for about 16 of the 36 in the most recent graduating class. 75% of Ruby's clerk compared to like 12% of the remainder of the class. I went to a giant public undergrad, so maybe that's why I find the hand-holding and favoritism a bit strange.
The class they had me sit in on had a worse professor than the ones I saw at Berkeley, NYU, and Harvard. But, on the flip side, students do seem to have ready access to their professors and will stop to chat with them in the hall.
Re: outcomes - looking at overall outcomes for the school doesn't make sense. My ability to succeed is not correlated to the average outcome of a Chicago or Harvard student. It's far more up to me and how hard I work to get top grades or how much effort I put into cultivating relationships with professors and taking advantage of opportunities. Both schools have the ability to help me make connections with judges and employers, and both schools are well-respected enough to serve me well. Once I'm there, my stats no longer matter and it's up to me to make the most or least of my time.
To answer the question, I like Harvard far more after visiting but have still not collected and looked over enough information to finalize my choice.
Regarding the money, none of you seem to evaluate debt in the way I do.
The Ruby is not money in my pocket. I will be low enough income after Harvard that, over the 10 years after graduation, Harvard would very likely be paying at least the value of my Ruby (likely more) on my behalf to pay off my loans. At UChi, I'd still leave with about $50K in debt. There's a very real possibility that I would not be in LRAP qualifying employment (by Chi's rules), so I'd be paying that $50K back myself on a salary low enough to make a 10 year repayment plan a bit difficult financially. If I couldn't afford the 10 year plan, I'd be in the shit land of negative amortization and would deal with the tax penalty at IBR forgiveness. My $50K in debt would balloon larger, and I'd be on the hook to pay it all off. (Or a good chunk of it, depending on how much time, if any, I was in LRAP-qualifying employment). Even if you qualify under Chi's LRAP, they only bay IBR payments, so if you want to avoid negative amortization, you're gonna have to fork over more out of pocket.