@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 ***.

It was painful but absolutely worth it.

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.

Lack of maintenance was a bit of a pain toward the end, but it was also great to have dirt-cheap rent and lots of freedom (wanna paint the walls red?

My gut feeling is that these people will be a pain to deal with.Do I even need to provide a reason for denying them?

What are their pain points?

Here's the painful truth: that kind of info isn't readily available.