If you’re placing a new property into service, you can discuss cost segregation studies.

Philly is a nice option, but you have to study the blocks for about a year to be sure you understand the area you are investing in.

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

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

Study the market.

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.  

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.

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