The people who live there typically sign strict lifestyle contracts that state they have to leave immediately if they don't follow it.

Property management is a pretty painful industry similar to general contracting... no one ever calls to tell you how grateful they are that the heat is working lolHere in Illinois, the answer is yes or you at least need to have a managing broker on your team as JW mentioned above. 

You're depending on one person's opinion of the value of your property.

Are online webinars as good as in person meeting? 

You could even negotiate into the contract that if the neighbors qualify you don’t have to pay the full leasing commission If needed some cash you could always do a cash out refi and take a small amount out.

Your accountant/cpa will be the best person for to advise  

I was selling my personal home.

I was selling my personal home.

My personal opinion of values is that if you're looking to get a predictable return on investment that you would be better off buying a legal duplex.

Have a calculator that shows this as well.What is boils down to 99% of the time is #3 and that persons ego / fear of giving someone else $.