@Victoria Knutson start by defining your primary goal and then quantifying it.

Never done this before so looking to hear more about deal structure and how to actually quantify the cost of carrying the loan.

I pay my CPA something like $2k per year but I can't even quantify the tens of thousands of dollars that he saves me every year by structuring my tax returns exactly the way that they should be. 

I think that could be difficult to quantify/ qualify & could turn future tenants off if they think they are going to be fined X amount of dollars if they are out of town & not able to notify me of any "utility" work being done.

Better tenants and less vacancy is near impossible to quantify when making these decisions, but the anticipated benefits do exist.

The numbers typically look great on paper but there are other factors that come up that are hard to quantify. 

Does my projected and expected ROI factor into this and how would one quantify that for deal analysis.

If you've got a commercial property you're checking out, the first thing would be to quantify how profitable it currently is(if at all), and then what the future value of the property may be.

Quantify the repairs — once you know the cost you can negotiate where you need to.

I plan to withhold money from his security deposit, but am unsure how to quantify what should be with withheld.