This is incredibly important work and in order to create the most impactful and transformational program possible, I am looking to interview people who fit this description and learn more about their challenges, frustrations, dreams and goals. 

Good property management is the challenge.

Hey Bryan, I have 12-doors in Detroit that I self-manage from California.Yes, the extra cash flow is nice but I also don't believe anyone is going to manage my properties better than I will (even from afar).The biggest challenge I have as a remote self-manager is doing turnovers.

If you’re up for the challenge buying a new property to house hack every year or year and a half is a great way to quickly build a portfolio.

But there are other factors of a personal nature that will dictate when people want to use leverage or not.

@Michael Schaffer  Gas stations present some unique challenges. 

I did speak with a property manager in the area and their biggest challenge in Pueblo is finding qualified tenants. 

CT requires an Architect (or Engineer) for projects of this nature, especially a building of this age where it's likely there's structural/framing items to address.

Securing private funding can be challenging, especially when you're just starting out.

They naturally value it at it's cost to them, next to $0.