Schools are solid, demand is high, and I think that you'll see an increase in housing prices in the future.

I hired Jenny Yi to design our latest STR in person, she demanded that I pay the full amount of her services upfront, $7,500, which I thought was strange as we are used to paying half upfront and half once it's completed, but proceeded anyway because a couple of people recommended her.

Neighborhoods like Logan Square or Albany Park have seen growth in rental demand, making them potentially good starting points.

I could keep it and rent it, rents are good and in high demand but just looking for a different property type. 

Cheap homes for an area are cheap for a reason - low to no demand from local investors or owners. 

there is tremendous demand for inventory by both investors and retail buyers which is making it tough for the casual investor to succeed.it's great that you're thinking about getting your financing in order. 

As @Robin Smith mentioned, for assessing demand I used FurnishedFinder.com/stats; you can see demand data for a given city and some pricing data too.

Increasing for times when there is more demand and decreasing when it is slow. 

Be sure that you're applying whatever late fee your lease allows to every late payment and demanding same from the tenant.

Fixing up a property and turning it into student housing is a smart move—steady demand and solid rental income.Great job!