Thanks to the sharp eyes of a Claverack resident, I just became aware of this amazing, searchable database at the Times-Union’s website—which allows you to track what people are paying for property taxes throughout the state.
Here’s the link just for Columbia County, showing the top taxpayers in descending order. It starts with the Top 50, but you can continue as far as you want from there.
One thing to bear in mind—some of the taxes listed are hypothetical, in that the Property Tax Tracker includes nonprofits, but does not identify them as such. For example, I don’t believe the Fireman’s Home in Hudson pays $600,000+ in property taxes (nor should it); that's just the amount they would pay based on their assessment, if it were a for-profit entity.
(Also, it’s not clear whether in all cases the taxes paid by the owner of multiple but unconnected parcels are linked; for example, if you owned a house in Kinderhook and a building in Hudson, would the taxes be combined for ranking purposes?)
Assembling this data must have cost the T-U thousands, maybe tens of thousands (though some counties, such as Dutchess, charge far less for assessment data than others; I once paid $5 for the complete Dutchess County residential rolls on a CD, info that would cost hundreds in Columbia). I’ll be doing some sifting of it over the next week or two.