Should get interesting, lot of WEALTHY and connected people.

My clients are ultra wealthy and they do not want to be bothered with anything.

one thing I see is in these bigger cities in the mid west much of the urban core is more renter dominated than other urban cores.and landlords are doing a better job with their work so you don't see as many failed landlords or burnt out landlords as in the past. so that inventory is not hitting the market  Jay that is certainly the case for Milwaukee, landlords are more educated, probably also because of the good work people do on BP and locally, the Brew City - full credit to @Rebecca Knox What puzzles me is that I see the same hesitation in the wealthy suburbs, 350k and up.

The property I am attempting to buy is in a very nice wealthy neighborhood in central Illinois, however, It doesn’t have a single renter occupying the property at the moment.

So let's take a step back and first consider how long it normally takes to be wealthy. 

I would love to truly tell my 4 kids that that can go and do anything they want and be anything they want and go to any college they want to pursue those dreams based upon the wealth I have generated through REI (or other investments). 

the wealthy landlord knew this was an inherent danger but failed to install a railing to cut costs.

It was built by a wealthy Philadelphia doctor in 1891 as a wedding present for his son.

It will demonstrate the benefits I alluded to aboveWhy the Wealthy Put Their Money Into Multifamily & Commercial Real EstateAnd here is an article I wrote on why I like properly structured debt on real estate investments. 

We'd rather be wealthy in our free time and travel.At the the very least if you want to buy a new car find a property that will pay for it.Good luck,Casey