We have a condo that we plan to keep as a rental and start building a portfolio.

I lend money privately and would never consider this as it is dependent on things out of my control (permits, neighbors, you being a good host, rental demand etc) I sell a ton of STR that are in actual resort communities and have great amenities and they are all  competing for the same guests, I can't imagine that there is a need/demand for this type of unit.

Assuming that the units are the exact size, you taxable gain would be allocated 50/50 between the owner occupied unit and the rental unit. 

The last rental I posted, I had a woman apply and found out she had stolen someone’s identity when I was working through the background.  

Long/medium/short term rental?

The city's diverse economy, favorable tax environment, and high quality of life attract a steady stream of new residents, ensuring robust rental income and long-term growth potential.

I will have to self-manage like I do our rental in Hawaii.   

I'm Eric - my wife and I are exploring purchasing our first rental property, ideally in the Pittsburgh area (especially the South Hills).

I am seeking advice on the most ideal location in terms of ease of renting, a strong rental market, and potential future appreciation in value over the next 5-10 years.

Egress will be required and depending on your municipality you may need rental license or permit.