I would study the listings from the top performing rentals in your area to see how they are overcoming any challenges with location.

Tenants in many markets already believe they pay too much (contrary to recent studies that show rent to property values have never been lower for the large US cities).If my insurance costs are not double my current rates over the next couple years, I will be pleasantly surprised.  

In addition to other tax strategies like a cost segregation study on the fully rented out house.

Tangible personal property identified in a cost segregation study is what allows you to accelerate depreciation.

I’m most impressed with the fact that you studied real estate and real estate markets for a year before investing; that you scanned the possibilities, chose what you considered the best opportunity, and went all in.  

Study the market.

I'd love to learn more about investing in hotels and this type of properties, so please if you have any books/documentaries/any type of resource that I should definitely study before I venture in the wild, comment them below my post.Thank you so much in advance!

Perhaps do a case study with a hypothetical deal you think is typical for what you are looking at and compare it to the alternative investments you might use and their expected returns.

Since you're so close to Loyola and not too far from Northwestern, I imagine you might have a pool of people who need temporary furnished housing while they study, do a medical rotation, or travel in the medical industry.

"when you study for your real estate license.. the study materials go pretty deep into the Law. and then Ethics and that the two are not the same..