As that date approached and I was told we would not meet the March 14 deadline, Jason was unable to provide a firm closing date, despite repeatedly assuring me that my file was being worked on.

I can assure you a powerful older female is just as capable of doing this to a young man.

@Diana Reinfeld As a listing agent, as well as an Investor myself, Sellers generally feel more confident receiving an offer from an Agent so that there's more assurance that nothing will be missed and handled properly, and actually listing agents generally end up done more work that would generally be done buy the buyer's agent so the listing agent would also rather receive an offer from an agent vs. an investor. 

Your coming on here truly looking for assurance, certainty of a direction being "the" direction and truth is, there isn't any.So, do the only smart thing, to get that certainty. 

But, rest assured, we do it everyday. 

I assure you the if there was a recession to rival the GFC, I am in a position to come out fine.In addition, it is best to take risks when you have little to lose.  

A very small price to pay the assurance or funds to your closing costs to repair the line or whatever you need.

Generally, if you have a policy you can be assured that no issues will pop up later that will prevent you from selling it or refinancing it.  

In some counties, this can mean unexpected delays and additional legal fees before you get access to the property.But as the market assures, a thorough due diligence avoids or lower the risks of these situations...

If that's the case I would not at all be assured of a court victory.