Tenants and growth potential-  Any thoughts on "the heights" and whether the area still has room for appreciation? 

You need to think about not just the potential income but also the potential problems such as city ordinances, state law, insurance, potential eviction issues, etc.

We're still seeing positive cash flowing deals here and lots of potential for appreciation.

I think there's a lot of potential when it comes to Kenwood/Bronzeville.

From there I'd look to refi and use the cash to then acquire STR's or potentially bigger multi-family/apartments.

Right now the majority of viewing requests I am getting are from potential tenants that have credit issues and eviction filings.   

While we both have strong W-2 incomes, the large number of properties I own has made conventional lenders and agents caution that securing a loan for our primary residence could be a highly complex process.I’ve consulted with some local banks I work with, and one has expressed potential interest in financing our primary home.

The current use of the property as a two-family dwelling significantly impacts its value and marketability, which is distinct from single-family homes.The initial appraisal comparing your property to single-family homes is likely an oversight, as multifamily properties are evaluated differently due to factors like rental income potential and investor interest.

I am afraid we will fall for a property with a false sense of a good deal.Are there any suggestions to help me run an analysis that would better account for the larger down payment and allow me to better analyze potential properties in the future.

Many of my deals were priced properly, but often the seller or market can't for various reasons see the potential in the property.