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

Don't forget cost segregation studies as well. 

Study the market.

If you study on your own, you will have gaps, but you may end up with $25,000=$50,000 in real estate. 

You also want to see a reserve study and only invest in a property where the HOA is at least 30% funded, less than that is assessment territory. 

Lost time-  you don’t find this out till your Geometra does his study.     2.  

But, selling “cash flow” works for other industries, such as oil and gas production, music royalties, tv syndication rights, and probably some more I’m not aware of.  

Study the market.

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.

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.