We did this once for one tenant in the height of the recession.

Chicago, Woodlawn, Calumet Heights, Deering, Northwest Indiana, 

I'm out of Arlington Heights.

What would a 3 bedroom that is bran new inside rent for in Jersey City Heights that's around Charles St. between Summit and JFK Blvd?

One section of my building needs to have the shingles replaced and I will be using a contractor to do that job (due to the height of the roof).

That may not apply if you bought at the height of the bubble.

For my money, you either go with a long time gainer neighborhood like the UWS (high but not outrageous prices, good inventory, perennially desirable without too much trendiness) or somewhere on the upswing popularity wise (right now I think Harlem and Washington Heights are hot, with lots of new development and businesses going in).

Same with using comps in North Park or Burlingame for properties in City Heights or Golden Hills.

I am looking at property in Alexandria to Vienna and Captial Heights to Oxon Hill. 

I have one of those Pilsen-style 2 flats where it's "sunken" below street level and there's only about 3 feet of height in a crawlspace below the first unit.