@Aaron OCallahan
It's a good question. I think Poughkeepsie is getting to be on the high-side of values as well. Especially when you look at balancing the risks such as new NY Renter Laws, high taxes, and lack of business growth.
I think there is upside with the new hospital opening up soon, Marist adding a medical teaching program, easy access to metro north, favorable pro-growth government, etc..
I've run some #'s for Poughkeepsie and nothing seemed to cash-flow enough for the risk, however, I've not dug deep into off-market deals, which is where you are going to have to look.
I've pretty much given you a non-answer... I'm sure there is money to be made in and around Poughkeepsie but you will have to dig and work hard for it.
@Eric Hrlbock and @Matt Caven seem to be active in the area and there is a Facebook page for a local REI (I just found this when searching for Eric's name)
If you come up, I'd be interested in walking the area with any other investors out there. I'm right across the Mid-Hudson bridge so it's a 2min drive for me.