House-hacking/having roommates is a tried and true method of building wealth as old as the hills, within which the property owner has a lot of control, low risk, and reasonably quantifiable returns.

Fortunately, real estate valuation methodologies are well defined and there’s ample sales data to quantify any acquisition these days.Buying decent properties in solid locations at a sensible price is pretty straight forward.

@Todd Rasmussen You'd have to get proof of deposits or quantify that risk in an allowance from the seller at closing. 

question two if we ask for a discount, how do we quantify it?

HVAC's our sub bought 60 HVAC systems and put them in his warehouse to make sure they were good to go for the rest of our houses.. cant quantify those type of relationships..

They want to generate the highest possible returns relative to a quantified level of risk.

On a large scale like you are discussing, I see the benefit, but to your point...how do you quantify that ROI on the charger install?  

It may be worse than expected but hard to quantify. 

The confusion is there because growth and expectations are almost impossible to quantify. rent growth of 5% forever, sure why not?

Since you do not realize principal until a sale its hard to quantify as monthly income, however, since you will get that money back at a sale its not really an expense.