On you question, I suggest monthly updates until you have something live. But if you post your list ("ton of things") of ideas, we could comment on them specifically.
By the way, I like your business concept. Except I'd remove the Chicago-specificity from the tag line, as I would assume you can probably scale this quickly. If you need to start with Chicago, put that in secondary text on the front page.
Advice wise, we've found that the pages work really well, and not just for us, but it does require for you to spend some time thinking about the design, your messaging, and more importantly, how you'll get people there in the first place. It's kind of an amplifier of sorts.
Anyway, we'll have some great data to share, but we're just trying to get to/through SXSW right now.
I'm glad you like the business concept. The way the current system is being set up, is that you can list your parking spot from anywhere. We are focusing all our marketing efforts/energy/time in Chicago to start, but it can scale and be used anywhere there's an open parking spot.
If having the "Chicago" there puts people off from other areas, I think you're right about removing it.