What would be your first purchase if you won the lottery?
I'd pay off the car, take a vacation or two, and buy a condo or something. Possibly in Chicago. I dunno. I like my job and my coworkers, so maybe I'd just buy one in Milwaukee itself. Someplace with a shorter commute.
Also, IAWTC that two condos is definitely the way to go. I know of a great real estate agent who would totally get you a great deal. :P