Wow! Thanks everyone for such a great response!
As to some of the specifics people mentioned...
My daughter is just now taking SATs. She is not particularly self-motivated about school work, which is a big reason why I'm starting to ask around about the schools she is interested in. I am concerned that if she gets into a self-directed program she will just get lost. She does much better with well-defined structure. The structure need not be conventional, but it does have to be there.
The drug and alcohol environment matters very much to her. She identifies with some of the straight edge/hardcore punk scene (no drugs, alcohol, etc), largely because in our large urban high school, it has been hard for her to socialize with kids who aren't doing drugs and alcohol because there are so few of them. She never goes to parties, because of the pervasiveness of drugs and alcohol. She does give a pretty damn good party though!
We are looking at Macalester College--thanks for the mention of that one! Yes, they are very well endowed. And U of VA has been suggested for the same reason. But what I don't know about Macalester is the structure of the academic program.
I'm glad to hear there are folks here with experience of COA. I'm wondering if it will be worth a trip to visit the school (we are in the Midwest). It seems to have an alternative academic framework, but I'm wondering how structured it is? I like Antioch because it seems to be pretty structured despite it being unconventional.
We haven't looked at Oberlin--we'll give it a look now though. And where is Deep Springs?