Wow, lots of good information and lots of food for thought.

And it could be attractive to out of state talent with an impressive food, music, and art scene.

Food not covered if power goes out all food in fridge is lost. 

We were professional chefs and restaurateurs for many years and would be happy to invite (bribe) people with food and wine in exchange for real estate help.

Tenant of 2 years moved out and left the place barely broom clean, but with food and dishes in the kitchen cabinets, lot of nail holes in the walls, the floors in dire need of mopping and marks on the walls.

It is a necessity like food, but nobody ever says buying groceries is throwing money away.

Does anyone have any experiences with the Cook County Land bank--purchase process, deed restrictions, etc?  

With rooms you have the added expense of utilities, as you said, but also the added management of conflict resolution, utility control (lock box on the thermostat and making frequent visits to inspect), common area cleaning, theft of food, more traffic, etc.After doing the math, a good tenant is more stable and cost effective than renting rooms.

By having a PM run a property you are living in you will run into the "too many cooks in the kitchen" syndrome.

I wanted to start a business, I spent about a month researching food trucks and other like ideas for cash flow and retirement.