I'm a retired engineer and have been successfully using income from these houses to support my retirement without dipping into retirement savings.I'm transitioning my business from rentals to a franchise and would consider selling one of my houses (5 br/4 ba - the other houses my son while he's still attending).

It's usually best to talk with your neighbors about your plans and get their support as one of the variance tests is that the requested relief does not cause a public health issue or alter the essential character of the neighborhood.Try googling "tests for a variance in [your state]" and talk with your local zoning department.

A link to FilePlace is at the bottom of every page, making it easy to find.If you have technical issues, email support@biggerpockets.com, and someone will help you.

Clarify your strategy—whether it's rentals, flips, or house hacking—and build a team of agents, lenders, and contractors.

Additionally, I'm working with the RE Ally Property management team, who was able to find a tenant to rent at slightly above market rates without any vacancy.

I have a team and large network of wholesalers, contractors, property managers etc.

I told them we sent out a ghost detecting team and found 0 ghost. 

I have been on board with an all military affiliated team with Coldwell Banker Vanguard;The Military Group for about a year.

Cashflow, ability to build a team, landlord tenant laws, price to rent ratio etc.......were all factors in the decision making process almost a decade ago.Now,  I wonder why your approach is an either or view? 

@Jacob Dalton, I'm going to have to agree with Jonathan Klemm (sorry, couldn't tag you) & @Brie Schmidt -- you can definitely be a successful landlord in Chicago with the right team in place.  1000's of investors do it every day.