On the PCR, it says the HVAC condition is ok but not functional, could not test plumbing b/c it was missing 2 feet of copper in the basement, and water heater functionality failed with decencies noted.

Yield is a function of risk. 

I believe I can purchase the property for $150K and it is going to take about $500K to white box and make functional. 

@Mark Horton II check out Pints & Properties, second Saturday of every month, 3:30pm at rotating breweries.

I know that zillow has some of that functionality but it only goes back 10 years so for example it's not possible to look at data from the last market crash, which is exactly what I want to look - get an idea of worst case scenarios.

I agree. it seems like the flippers function does not work.

Use the search function my friend. 

So my money is wrapped up in a 10 year functioning business with deep wells of skilled trade workers.

Given property prices are a function of rental income multiples, a real estate buyer should be looking to buy at similar pricing discounts from peak rental periods.

It is a function of limited supply and steady demand (some would say increasing demand).