Every small city in NY State is an absolute dump from what I've seen. Not familiar with Amsterdam but Poughkeepsie, Troy, Utica, Newburgh, Monticello, Niagara Falls, Utica, Schenectady etc. are bad. NY State has a lot of natural beauty but if you didn't know any better you would think you're in Mississippi.
Whatever the topic, superjohn, you come up with some of the most uninformed comments going. Congrats.
I am from Colonie - the working class suburb of Albany. My Dad, a UCONN BS MS Pharmacy, landed as a Professor at the Pharmacy college in Albany and had a 55 year career. Myself, my daughter and about 10 cousins (the family is from Derby - Shelton - Southbury) enjoyed our years at UCONN; we are stakeholders and true blue.
Today, I work in real estate with projects in Albany and Hudson NY ... and Baltimore and Atlanta. Student housing parcel just went under contract in Chattanooga.
For me, the most compelling thing you can say about Upstate (Westchester people - where I live now - say it starts at the Tappan Zee (not Mario Cuomo BR) is the move of NYC money up the Hudson. This is also true of Stamford and Greenwich; Rye & White Plains & Scarsdale. It is true of NJ: Bergen County and now the amazing transformation of Asbury Park. In Hudson NY (formerly the Albany area center of whorehouses and drugs - see pre 1990) you could buy 1860-1910 houses for $90k in the 1990s; today they are selling for $1.2 to $1.9m. Why is that? It is the young people coming up on the train from Penn Station (Brooklyn or Manhattan) seeing value. The Airbnbs (there are over 170 of them in Hudson - a city with normal population of 7400) are highly priced. The counties Dutchess (I guess you exclude Poughkeepsie) to Columbia to eastern Rensselaer to Berkshire ... to Litchfield CT are all seeing slices of this. Culinary - Wineries/Breweries - Home Goods (lots of internet focus) - Art - Music. The Jitney that only used to go to the Hamptons now goes up to Columbia Cty. Westside Manhattan wealth are buying near Woodstock.
There's not much going on in Connecticut beyond the same pattern. I love Rochester; I love parts of many upstate cities. But the real engine is the wealth seeping out of NYC. That's probably similar to NH from Boston; Delaware from Philly. Both Toronto & Montreal are booming; but few (other than Burlington VT) feel that.
Amsterdam? Used to be mostly Italian & Polish when I was a kid (hmmm sounds like Derby); today, it is Hispanic. Rough? Well ... immigrant and it's developing.