"An ounce of prevention is worth a pound of pain."

So, in my opinion, they are feeling you out for a discount, in which case, since moving is a pain, there's no reason to give them the discount... unless your rent is on the high side and if they move you will not be able to fill it at the current rate.

I feel your pain Cynthia.

I was working for a large syndicator at the time... ( this decades version of a crowdfunder). they had about 150 GPs set up and 1 billion in assets.The investors came in as different class... doctors taking all that tasty depreciation.. retired folks taking the cash flow and middle of the road folks taking half of each.. each GP had 3 class'swell tax reform made the exit very painful and really put a wrench into things at that time.

I would take the pain now.

The end game is that we are now out the $6,200 with no relief coming from insurance.  

I have bought two houses the "traditional way" and it was painful to say the least.  

@Casey Gray if you can get a conventional loan despite the property's condition then the only advantage you have is that it will cost you much less, but that's at a price of it taking a long time to close, being a pain in the derriere, and possibly costing you the deal because cash is king.  

Is the messiness of the communication indicative of bigger problems and setting myself up for a world of pain with the tenants, or am I overthinking that and its really just a problem of elderly owners with their son trying to help sell a property in an area he doesn't specialize in?

I hear you, mailing campaigns are a pain in the ***.