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.

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?

Ugly things happen when money disappear and you start talking in negative numbers.Good luck.

Ok, all kidding aside, this sounds like it could easily just be a misunderstanding of the loan terms, or it could be that the loan is totally legit and you will see 100% of the money, but the lender just thinks they can get one over on you and make a few extra bucks on fees, and then it could also be a total 'take your money and disappear' scam.

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.