If it was city ROW, not sure how one could quantify $$$ damages for a claim.  

I hope you're right that with a bit more experience it will be easier to quantify someone's value.

The value that is hard to quantify if I use scenario 2 is not using any of my resources except to do the repairs

I'd come up with a process to interview property managers and quantify your findings so that you could make an informed choice, should you choose to invest in RE.

Mary Ann It can be convoluted when quantifying whether it is commercial or not and can be quite the mind job if you allow it to be.

As to Mr Prominent's opening ideas, to mention "risk mitigation" and then follow with stating loan risk can not be identified or quantified leaves us with a bit of a dichotomy.  

I agree looking at gross rents and operating expenses is where I would start in comparisons of alternatives, but looking for a way to quantify the comparisons with a summary measure.

I'd start by quantifying what type of asset you're searching for.

@Kurt Gardner and @Aaron McGinnis, that's pretty much the way I've been leaning - it's hard to estimate those "quiet" costs of slab installation... that would require more time and experience to truly quantify.

They don't know anything about real estate so that is the only way they can get a quantifiable representation of value.For the future you might look into 5+ unit investing.