I have an opportunity for a solid STR in the Catskills of New York, but it has a few hurdles.  1.

Upstate for us doesn't really start until the Catskills so not sure where you're looking to buy.

The Adirondacks, Catskills, and Fingerlakes are tourist regions.

I've been looking to invest in upstate NY in areas such as Rhinebeck, Catskill, Hudson, Newburgh, Saugerties, and Kerhonkson.

we rented a air bnb in the catskills it sucked.. but my son in law rented a semi mansion on the same trip on the shore in Mass or Main or somewhere up there and it looked pretty cool..

I've been shocked recently on two separate vacations, one to the Catskills and one to the Finger Lakes, how many "for sale" signs there are up there.  

Looking into the possibility of a few higher end homes or a small community of townhomes/condos.I have years of solar development experience, but have yet to get involved with RE development, so I am looking to connect with any sustainability focused/ LEED developers in the upstate region surrounding Hudson/Catskill or Great Barrington. 

Any thoughts on Catskill, Cairo or Athens? 

I've been thinking about investing in the Thompson, Monticello, and Ellenville markets as we approach the opening (Tentatively March 2018) of the new Sullivan County Casino: "Resorts World Catskills."

I run a 2 bedroom cabin in the Catskills area of New York (2.5 hours from NYC) as an AirBnB property, so my market is a bit different than yours.