He said if this guy manages to find a buyer, when he approaches us we'll squeeze him in the middle and make him overpay to close the deal.

So what I wanted to know is how should I approach the listing agent and negotiations?

They are the key holder.I suggest speaking with a lender and getting a clear idea of what you qualify for and what the best approach moving forward is. 

Very approachable price points and small consistent returns every month aren't something to overlook! 

Should investing be a different approach ?

If that approach does not work, I am not sure if I can pursue a normal foreclosure procedure with notifications to heirs or need to do something different. 

They may surround themselves with others willing to take on the more mundane tasks they used to do but they're constantly forging ahead into the next challenge.The way people view or approach something is crucial. 

Any advice on how to approach this situation.

I know trying to time the market is generally poor advice and more gambling then investing, but I am hesitant to start investing in a Roth now when the market feels like it is approaching a peak.

My approach is more of a "poor mans" variation of this same strategy because I'm looking in less expensive "up and coming" areas, as well as still doing much of the rehab myself.