I started real estate investing by house hacking and then getting into rentals from there.

And on the houses I build I pay the lumber direclty myself I pay the roofer..

It’s just like having your 5 houses, only all in one building.

It’s a larger house (3500 sqft. 5 bed), but is secluded, private, centrally located, and sits on nearly 3.3 acres of the East Bay Hills, with open space as far as the eye can see outside.

The contract was a simple 3 page one and I wrote this in.Also, it is a single family being rented as a rooming house (which is technically not legal here).

Section 8 may seem like a home run but I've seen houses destroyed in a years time, I would steer clear. 

My friend is selling his house and is open to an assumable mortgage.

Essentially he wanted to live in his own place but didn't have the money and I figured buying a house with him at the time was a good investment.

The fact that you are asking this question of strangers instead of your PM indicates you have an amateur managing your property.

If you ever have questions on landlord software or student housing, I'm a great resource!