You have to issue notice to enter according to your state law and go in...deliver a month worth of notices at the same time, change the locks so you have access, and get done whatever you need to...you can work every day...we install a permanent lockbox with keys at every property after we change the locks...no barriers to entry for contractors...I see this a lot where people work around their tenants....if you lose control things will go downhill rapidly.

We are interested in a property and the driveway is maybe 25% asphalt from the street and somewhat down hill.

There are some parts of the Poconos that have gone downhill a bit, while there are other areas, especially near lakes or in gated areas that are doing great. 

Like @Lorenzo Wright said, this property could go downhill quickly, and I think you need to mitigate the risk by negotiating repair for the larger items by the sellers. 

Sometimes the best deals you make, are the ones you don't, and I can guarantee you this, when you start rationalizing, or getting emotionally tied to a property, you're heading downhill from that point forward.Not enough info ($$$$$ numbers) to really even understand the true/complete picture here.

I’d also consider potentially the 80/20 rule of selling off your worst (you decide: lowest cash flow, biggest upcoming CapEx, neighborhood going downhill) 2 and rolling them into a smaller multifamily (4 doors / 1 mortgage) through a 1031 Exchange. https://www.biggerpockets.com/topics/877606

The quality of renters have gone downhill also.  

Learn to ride a bike on a flat surface before attempting a downhill backflip.

It is more like a snow ball rolling down hill. 

If you hire a property manager they are going to hire a $15/h service and everything goes downhill.