I would take the pain now.

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?

Those look sharp, @Pavel Ushakov  Thanks for the input.

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

It was painful but absolutely worth it.

I don't just expect things for free, I am willing to also provide my experience in owning several different successful and Horribly unsuccessful businesses for your own feedback, Have been involved in wonderful partnerships and THE WORST KIND TOO, I have good contacts in the construction industry and own many pieces of concrete pumping equipment and real estate, along with a sharp mind for numbers and willingness to exchange information and network.

Fix what comes up on the inspection or anything that is dated like old toilet valves that are going to be a pain once a tenant moves in.

Aside from how painful it was to get our real estate agent to prepare a satisfactory lease that protected us (she said it was compicated), she told us that according to the listing agent the sellers felt the rent was too high because it was more that their current mortgage.