Challenge link: very strong - a nice idea, well executed.
Image critique: subjects are very appropriate to the challenge but you are a victim here of poor, flat light (but if, like me you've had bland or poor weather then I understand!). Strong composition lifts this out of the ordinary with great DOF.
Out-of-challenge appeal: a bit bland overall (just the damn light really!) to hold me for long.
Interesting juxtaposition of two eras of architecture. The sky is the only disappointment here. Composition is a real grabber as are all those little squares.
Whilst I like the way you've fitted these into your frame, I eally do find the completely burrnt-out sky more of an annoyance than a useful contribution: the image becomes almost more about that white shape than about the architecture.
I like the Water Tower area of Chicago and this is among the best pictures I've seen of it. Great capture. I especially like the white areas to the right and at the top. They set off the subject well. The counter point of modern and old works well. Good job.
Nice idea, interesting perspective... The gray sky probably helped the exposure (no harsh shadows), but I think the image would have been enhanced with a more dramatic sky. Still a very good photo.