Hi Joe, this is for sure an awesome question, so many different point of views, the problem I see with .co is this one:
"Sites with country-coded top-level domains (such as .ie) are already associated with a geographic region, in this case Ireland. In this case, you won't be able to specify a geographic location."
Source: http://www.google.com/support/webmasters/bin/answer.py?answer=62399
So if I understand this correctly, and you want to target real estate clients in the Chicago area (which I love and will be there for the U2 concert on July 4th) and over US/worldwide, a .co domain is probably not the way to go here.
There has been a lot of talk about .co (TLD for Colombia), same as .ws, supposedly "WebSite", actually West Samoa, so I would advice to make the obvious, look at your competitors, does anyone has a .co domain and are ranking in Chicago? are any of the top 100 results anything but .com? try different keywords just to check if there are any .co sites ranking in the real estate market.
Hope that helps!