@Zoran Domazet & @Will Barnard - not an expert, but being in Florida (where sink holes are frequent) and seeing "polyurethane to fill a void" (polyurethane being an expanding foam with little load bearing capability) makes me thing that we are not taking about a small crack in the floors/walls due to foundation settling, but something more vicious.

I am certain there are  plenty good tenants we are missing out on that simply don't have that kind of cash on hand.

What do the sightlines look like from the main road (easy to see, down in a hole, high up on a hill?)

I know of a bank that, in spite of the above, somehow interprets it such that they will not let ANYONE use a 401k loan, no matter what, even though that guideline is crystal clear (to me, at least) that you can (solution: I simply don't broker the loan to that bank if that's the scenario we are working with, and I'm not even going to waste time with them if we're doing something along the lines of what is being discussed in this thread). 

A sharp seller's agent will simply counter your offer at that price, so you may pay more than was necessary.  

@Alex Levich The one thing I would do before you get into landscaping make sure you validate that the pool has holes in it so that it can drain. 

In my opinion, that's better because it's more passive for you AND there's an opportunity for upside (within 12-24 months) simply by leveraging the sponsor's expertise with forcing equity.

You also need to be aware that custodians are passive in nature and simply process transactions at your direction.

What if any of these negative scenarios are simply perceived by the other party?

I simply explain to the seller that I will be improving the value of their collateral.