House he lives in sold for $480k back in 2010; homes on the street sell for $1MM+ I happened to go by his place last week to discuss some business and immediately noticed all of these factors, and others like the near-rotting window panes made of wood and the roof that needed to be replaced last year. 

So after I factor in costs for vacancy, man't, reserves, etc. if I am getting my desired # or better than I am in.I supposed I could also do the probate thing to hunt down off market deals in my area since MLS deal days are gone, but I search for the path of least resistance for my money and my time.   

Or two pickups lose control and take out external roof supports at two properties in the same week and just drive on?

I usually recommend the two hour rule -- either a two hour drive or a two hour flight. 

What about moving the drive way to the other side?

He seems totally fine with the drive but I wonder how similar situations turned out for some of you?

I also agree with some of the posters above that you want just go ahead and factor in property management into your numbers when looking at cash flow (even if you just use that extra 10% to pay down principle or reinvest).

After 3 years the drive became tedious and we just didn't use the house as much. 

(It’s about a 40 minute commute for me one way to drive here. ) I called around to the waste management company’s and none of them had a big dumpster (40 cubic yard)for at least a week or two.

I am still interested in the property but given the scope of the repair, I'd like to get a couple of estimates from contractors first so I can factor them into my bid.