Being a NYC resident (originally from Long Island), the price of entry in the area is on the higher end, so I've been considering some options in the NY Capitol region, as well as NJ and CT. 

Look on Facebook as well for local investment pages, you will find a lot of local investors that you can meet with. 

The other hurdle is to find a contractor, that is something that you can do as well.

I was a flipper in 2001 and did really well until I fell in love with this big country property on a river up north.

Selling an existing, well-performing asset has some risks.  

So I said, "well, if that isn't the path, what is the better approach?"

Well, of course - that's obvious - but most people in most places in the US are going to spend too much on their purchase because that's what's available.

This is a group of MTR investors who have small to medium portfolios, but we welcome new investors who are just starting out as well.

Based on the info in your post, my recommendation would be to turn these assets into well oiled machines and max out their NOI.

I invest in Richmond as well, through house-hacking and BRRRRs primarily!