Circle of influence.

Placement and maintenance of gutters and downspouts can often be the greatest influence on issues like this.

.), length of the desired lease, zoning, all of these can influence price. 

All these factors would influence my thinking/decisions in this regard.In my case, I'm an engineer who worked the corporate 9-5 for a while and I got good experience that translated into a transition into RE. 

Or someone that is nearby, not exactly in your area but has influence and a track record for success.

How do you suppose I convince or influence him/her to do so ?

I'd rather learn about what influences buying behavior than what makes Pavlov's dogs salivate. 

Learn how to talk to and influence appraisers

Have your main influencer (spouse if applicable) read "Rich dad pot dad" let them know it's just so they can understand where you are coming from.

When I think of Chicago, I think of over-price, over-regulated, city of corruption (at least 2 politicians in federal prison I think) that's located in a fiscally unsound state.