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

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!

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 just read a few other posts. if you don't know the difference between "eviction and notice of non-renewal" you have a lot of studying to do if you want to manage a property.

Quote from @Aaron Zimmerman: I would look for other ways to legally reduce income such as cost segregation studies.

Study the market.

The unique format of this event, which consists of high-level education, gamified networking, mastermind breakout sessions, case studies, group deal analysis, market deep dives, and peer-to-peer coaching facilitation makes this the most impactful local real estate investor group a real estate investor can be a part of.The foundation of the group is built around the belief that everyone in the room has the potential to change the world… however most of us never have the time, energy or financial situation to even dare to dream big enough.

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.

Study the market.

Study the market.