You have very right to be irritated, they sound like a PITA....

I know that there are more ways to skin a cat.

That is common and it does irritate folks all the time but that is the legality of it.  

There are 1000 ways to skin a cat and 100 ways not to.

Wayne, maybe 4, 5, or 6 extensions is reasonable to you but when you're told every week that you will close the following week, you start getting a little irritated. 

You're a nice landlord with a heart and it shows for second guessing yourself, but you will grow tough skin over time ;)Best of luck to you!

@Eric B. most of HML would require the investor to have skin in the game, only lend portion of the price (75-90%).

However this one was kind of irritating.

They have no skin in the game after the house closes, the insurer does.I would highly suggest, with the condition you suggest the roof is in (5-8 years left on a shingle might as well be 0 with a preferred underwriter), that you look at Foremost, Berkshire Hathaway, and or USLI.  

It also means the Buyer has more "Skin" in the game than just the Earnest Money Deposit ... which means he has just that much more of a reason not to back out.