While I think it would be difficult to quantify exact ROI, I think any exterior updates would obviously make your listing more attractive (depending on your market) and therefore would therefore justify higher occupanacy and ADR.  

This is where option 1, quantifying the returns following a refinance comes into play.

Returns can be quantified, unfortunately risk cannot.  

This I think, is perhaps what you are looking at as well...a personal comfort level with the amount of projects you have going on, and are looking for a way to quantify that comfort?  

A good feeling I guess but the goal should be quantifiable. 

My question is how do quantify the work completed based on milestone?

I could check google street view, but is there a way I could quantify this in some sort of way to be able to compare apples to apples? 

I could check google street view, but is there a way I could quantify this in some sort of way to be able to compare apples to apples?

I could check google street view, but is there a way I could quantify this in some sort of way to be able to compare apples to apples?

While this isn't the only reason a loan can do into default, it is also the easiest one to quantify for lenders and borrowers, which is a major reason there is such an emphasis on this aspect.