Hello Thomas,Thank you for your input and showing me the numbers to quantify the loss. 

I can very easily quantify what my license brings to the table as I am sure your contractor friend (or anyone for that matter) can.

Just trying to decide the best way to quantify a “good deal.”On a pure rental the metrics are pretty easy.

It is hard to give you specifics without the actual numbers you are referencing, but in general for a long-term play you want to quantify the intrinsic value of the asset. 

How have these risks been quantified so we can put it down on paper before we get into the project.

If he is looking to finance a deal the traditional way, he will need to quantify his monthly debt obligations and make sure he will meet the criteria for the debt to income ratio for a loan.

It's part of the reason there are so many answers to this question...my only suggestion to you would be to play out some of the out there, scary scenarios (in a quantifiable way!!) 

I wanted to do an objective analysis so I figured out what parameters were most important for a reliable, cash flowing market (Low price/rent, positive population growth or influx, and job growth) tried to quantify them in widely available statistics and put them all together for the major (and some data for minor) metropolitan statistical areas.  

I don't know how to quantify that other than the estimate I've received from a separate contractor. 

It's quantifying "ample reserves" that I'm trying to figure out.I stumbled upon Brandon's Blog Post recently that has been very helpful.https://www.biggerpockets.com/renewsblog/2015/10/13/real-estate-capex-estimate-capital-expenditures/