Multifamily giant Village Green CEO John Holtzman tells us there's a demographic that's grossly underserved in Chicago, a story we're hearing in many cities. They're the recent grads who want to live downtown but need rents that won't hinder the payment of student loans, he says. Village Green—which'll soon own or manage 11 high-rises strategically located throughout downtown Chicago—recently acquired the 147-unit 860 N DeWitt (built in the ‘60s), which will be rehabbed and rebranded to serve that market, featuring smaller floor plans and outsized amenities.

The 22nd floor outdoor Sky Park (above) will include a green wall, fire pit, LED movie wall (just be careful what you decide to watch in the open air), and kitchen. Cosmetic improvements should be complete in a year. Its recipe for lease-up with young professionals: a transit-oriented location (just off Michigan Avenue and Oak Street Beach); efficient spaces with the latest fits and finishes; and amenities like concierge services. On the development side, you can't think “if you build it they will come,” Jon says. The success of the firm's Randolph Tower and MDA City Apartments in the Loop was due to innovative amenities and rents for those priced out of the booming luxury market. Smaller floor plans (it's done 435 SF) are key. Since Jon doesn't get enough risk in real estate, he also races historic cars.