t2009 - thought I might have some of your answers, though not all. Please understand that I am no expert in Waldorf education, and it's been a long time since I was involved in the school. Some of what I am about to say is hearsay and certainly a bit biased, but FWIW . . . .
I actually was a student at the Chicago Waldorf school my junior and part of my senior year. Obviously, it was not a great fit for me, or I would have finished there. That being said, it's not something I've totally ruled out for DD in the future.
This is what I know:
From what I could see, the early childhood program seems amazing and is probably one of the school's strong points. But be forewarned - Waldorf is not for everyone, and I would recommend doing a lot of research about the methods and practices of Waldorf ideas. Some of them are certainly a bit "out there", as they say.
The grade school and high school are very unconventional as well, and again, I would recommend making sure that you are truly in line with the ideology of Steiner/Waldorf in theory and in practice. While some of the theories/ideals sound wonderful, it is important to be aware of how these things actually play out in an academic setting. Some of my fellow students had obvious advantages from being lifelong Waldorf students, but there are disadvantages too.
As for the specifics of the Chicago school, I will say this. Some of my favorite teachers (ever in my life, not just at Waldorf) left while or shortly after I was a student. There seemed to be some conflict in the staff, and the rumor was that the older teachers felt that the Chicago school was moving away from what Waldorf is really intended to be. Though this is just a rumor.
And as for financial aid, it really is available. My parents were given a pretty steep discount when I was a student, though still paid about 14k a year. My guess is that if you really seem devoted to the curriculum/lifestyle (and it really is a lifestyle), and it seems like your family will fit in well in the community, they'll make it possible for you. My feeling is admission will depend on this as well, and they'll really be looking at how involved/in line you are, more so than your LO.
Despite anything negative I might have to say, it is a truly warm and wonderful environment in many ways, especially for little ones. And though I did end up leaving before my senior year was over, it is still something I would consider for my daughter, absolutely, if we have the funds when the time comes. And if they'll have me back, of course!
Whew. A small novel about Waldorf. Feel free to PM me with any more questions!