A good inspection report will be your main guidance as to the issues of a home (flaking lead paint, cast iron plumbing, etc.) and whether or not they should be addressed immediately; with that information you can decide if a property is a green light or isn't worth pursuing. 

Waynesboro and Green County are areas that I have looked as well and been able to find deals that can potentially cash flow. 

@Kaleb Greene- Yes there are a few meetups I go to when I have the chance.

The property has had a string of mom and pop owners, has been neglected and lots of deferred maintenance, but great location, large units, lots of green space and across the street from an A property-There is 3/4 of an acre at the back that looks directly at the field and already has utilities and permits for 8 units.

@Shayne Mahoney You can pick a "better" tenant, provided that "better" isn't determined on the basis of a protected class.https://www.mass.gov/service-details/overview-of-f...In other words, you cannot pick the green client over the purple client because you don't like purple people. 

Hey @Andrew Moore, that area is much further east than my area of focus, but there are green shoots from what I've heard.

I own a 2 family in Union square myself and with the Green line coming in, you are sitting pretty. 

Check out this BP Podcast, "Thriving in a Multifamily Investing (Even in a Hot Market) with Michael Becker Sept 27, 2018" Then check the 54:30 mark on that episode or listen to the begging of this line of questioning Brandon Turner and David Green ask Michael.

The rentals are in Green River.

Have you read @David Greene 's book?