Make it quantifiable and realistic.

How does one Quantify the Value that was raised?  

If nothing else, this will quantify how bad you want the answer!

Generally speaking, I think it's a better call to follow the quantifiable metrics.If one of the tenants makes a fair housing claim and you can clearly show there was another applicant who was objectively superior, the claim will end abruptly.

One question I have is how to quantify something like "diversity of business types"?  

I get monthly payments in between and that is regardless of the number of days in the month.I'm impressed that you actually quantify the difference, I'd have to think for a while to figure out how to do that.

No way to quantify that on the tally books though.Jason

List of most roles that qualify: RE appraiser, Civil or Structural Engineer, RE Agent, RE broker, RE attorney, Mortgage Broker or Banker, Tradesmen, ArchitctQuestion for self: How could you QUANTIFY tax benefits of being REI pro?

Are there any experienced investors out there who can help quantify these risks and/or point out what one might focus on?

I can't quantify the value of that on a spreadsheet, but it does have value.