I agree with the statement, 'buy your 5th tractor first'. Make sure you have enough power to use your implements properly. For instance a 5 foot finish mower needs 25 hp to power it properly. This is 25 hp at the PTO, not 25 hp in the tractor. I have a 6 foot finish mower, on a 33 HP tractor, 29 at the PTO. It is enough, but I could use another 5 hp when the mowing is thick. A FEL is a must for around the farm landscaping. I would also suggest that you get an extra set of remotes for a third function. You will find that you need it more than you expect. Very helpful if you want a hydraulic top link, or a log splitter. Since you are in upstate NY, you may want to process firewood to assist in the cold weather management.
A friend of mine told me when I was looking that 'almost no one has ever said, my tractor is too big, wish I had bought a smaller one.'
If you are subject to large precipitation, a larger tractor will get stuck far less than a SC. Make sure you get 4wd. Plowing heavy snowfall takes a lot more power and patience than you would expect. Depending an how far upstate, a cab may be something you should really consider. It's not just the heat, it's the ability to keep the wind/ice/sleet from covering you and the controls. Even in KY, I have been plowing snow, only to see my dash board become completely obscured by snow/ice. My control levers became icy, and the engine speed controller froze to the dash, and was impossible to break free. (I had to go back to the shop and break out the heat gun...) I live on 7 fairly flat acres, and 33hp is not really enough. I get by, but if I ever have to replace the 33hp, I will look for one that has more capacity on the FEL, and around 45 hP. I do no logging, no tilling, mostly mowing, snow plow, and FEL work cleaning up after animals, or moving round bales.
Take your time, make sure to sit in several makes and models. Ergonomics will impact you more than you think. Controls that are easy to reach, and ease of getting on and off will be important, especially as you get a bit older.