Really cheap to aquire and almost doubles in value after he uses the bobcat to level it out....

Level up and run some numbers--maybe a different market will reveal itself. 

I have STR investors in Florida making 25% cash on cash returns, long term rental investors picking up properties directly off the MLS and cash flowing day 1 in various states, and house hackers completely removing their housing payment from the picture allowing them to save for for the next property.The beautiful thing about real estate is there are so many ways to succeed and a plethora of strategies depending on your comfort level and how active you want to be.

And look, I don't doubt the anomaly potential, the Malibu homes etc. but point is when we get to certain price levels the price moves outside "median" purchase viability. 

That will get you from zero to about 80% knowledge level.1.  

Once you have consistent, high levels of cash flow then consider the “company vehicle”.

Raising rents to market levels is a big deal and hard to do. 2.

I would add there has to be some level of human monitoring going on.

Your main concern should be whether these bedrooms and bathrooms on the lower level are legal and have the proper egress require for fire code and livability.

And the top tier agents have their ego at the deal level.