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.

It is starting to look more and more like the 70s and stagflation is becoming a real possibility as a result of fuel prices   For the data people out there, this a different set of equations, it brakes the models and is hard to quantify in a twitter feed.  

Likewise, many things that you add to a basement don't quantify to value because it is "below grade".  

Very small and that poses additional risk which is hard to quantify. 

There are a lot of great resources and forums as well as people you can learn from right here in the posts my advice is before you start asking for a mentor make sure you know what your end goal is with a time limit and a quantifiable amount attached to it only then should you identify what strategy will actually get you there once you know those things then you start looking for someone to help you if you don't know your destination of what you want and when you're going to get there you can't expect someone to help you because they may take you to where they want to go and their destination not yours

But it's hard to quantify the peace of mind that comes with outsourcing this (Yes, I am biased). 

The correct takeaway here is that leverage can be a powerful tool.It can be used by investors to enhance returns by intentionally introducing a quantifiable amount of risk.It allows investors to take on more or larger deals than they would otherwise be able to if limited to their readily available cash.