@Danny Gonzalez you hit the nail on the head.

(prorating utilities by tenant head count for instance). 

He has helped me out countless times when I get in over my head. 

At first we thought he was just incredibly incompetent and over his head, and we wearily gave him some patience to get his act together all the while pressing him for at least partial payment.

There are a few questions off the top of head. 

I intend to relocate to the Rapid City, SD region in April/May for work, and I plan to acquire a primary residence that could eventually be transformed into an investment property.

Flipping is about as least passive as it comes, so just make sure you wrap your head around how much time and management it will take to be successful flipping.For anyone getting started, I always suggest these 3 steps:1. 

I will make sure to add that, thanks for the heads up. 

I'd like some input on wrapping my head around a potential first house and if this sort of deal/rent makes sense.

I believe, off the top of my head, it's single digits of rents actually have rent reported to bureaus.