Oh, I agree completely. Feelings have a nasty tendency of getting in the way.

I don't know that I've ever been in your exact situation, and I think there's something to be said out of caring somewhat and getting some fun out of the whole thing. Additionally, I wouldn't give up all hope yet on Penny. The City doesn't seem to follow a quite a few of the rules of physics, so if you could harness any of their more interesting exceptions, including the "magic"...
I haven't had a need to study that in particular, of course, so I can't be certain.