If you are new to this type of investing, I suggest you pick up a copy of Lend to Live: Earn Hassle-Free Passive Income in Real Estate with Private Money Lending published by BiggerPockets.

I will be house hacking and living in the property.

The plan is to live in it for a cpl years so right now I’m assuming my best bet is a tricky FHA 203k loan.

I'm not too familiar with rural deals, as I've lived in major cities all of my life.

Continue living in primary and rent out second one?

The rent from the rooms came out to $1,600 so my client is coming out of pocket only $600 monthly to cover his living while owning an appreciating asset in a gentrifying area!

We're in the same boat with family living in one of our rentals.

I live in Hadley, MA and open to talking in greater detail with you anytime.  

I get a lot of questions from the CA & Socal folks about how life in the fast lane in Arizona is doing and if it makes sense to invest Out of State for them.I still invest a lot in Phoenix and I'm very comfortable...

The biggest obstacle to overcome by far, is not so much that you need to find clients (although believe me, that's also difficult and is a constant effort until you're able to rely on referrals from past clients), but the customers you interact with need to trust you with their largest asset as a seller, and for one of the largest purchases they will make in their lives as a buyer.