If they are truly in love with it, are enjoying their life in that home, and intend to die there then no amount of money is going to separate them from that house. 

Kevin R Moses - search for house hack or house hacking and read Set For Life.

Thanks Adam the lease is based on the Wisconsin Realtors which states the Following:During the lease term, as a condition of Tenant's continuing right to use and occupy the Premises, Tenant agrees and promises, unless Landlord otherwise provides in writing, as follows:10.

That is a distinction I could have gone my whole life and never missed. ;-) We can have lunch and I'll share the details. 

I'd also recommend "Long Distance Real Estate Investing" by @David Greene, "The Book on Managing Rental Properties" by @Brandon Turner, "Set for Life"  by @Scott Trench and "Crushing It" by Brian Murray

The goal of course is to keep those deferred tax dollars working for you through your life and then passed to your heirs tax free. 

Chicago has a lot to offer in terms of housing supply and quality of life.

Jeremy, is your property in a condition where you can not rent it to anyone else or sell it to anyone else?

I sent someone to assess the condition and they would not allow them inside.

Yes, i am looking for long term hold and rents, i dont have enough experience in rehabbing to do a flip yet, due to my physical limitations from my military days, i am striding to increase my passive income to a point i can comfortably live the rest of my life on.In regards to the %, i have no clue, i have gotten multiple comments to just go by the percentages.... with no additional details.