I want to focus (I think) on family-friendly higher end neighborhoods. 

They're a member of the Small Luxury Hotels of the World organization, which is not easy to get approved for - but which also now means they are on Hyatt .com (Hyatt just recently bought the Small Luxury Hotels of the World).

Don't buy in the roughest neighborhood in the urban core.

If you're gonna look at Cleveland, I'd say you wanna read The Ultimate Guide to Grading Cleveland Neighborhoods before making any buys.

A good PM will be realistic on what to expect from Section 8 and help you identify properties/neighborhoods that will support your goal.

One is fourplex near downtown of Union city new jersey and the other a duplex in jersey city heights neighborhood.

There are two condos in my neighborhood that are trying to sell, but have been on the market for 100+ days.

Knowing the three cities mentioned is important for grading the neighborhoods and can vary street by street. 

However if you buy in a neighborhood where people do care or all  your tenants have cars, you may get shut down quickly. 

That will allow you several benefits like adding the square footage to your property, having it appreciate in value as more ADUs are added to the neighborhood, legally rent it out within the city's parameters around long-term, mid-term, and short-term guidelines, and feel good about your investment.