I grew up helping on a small family dairy farm across the river from you in the Live Free or Die state; milking 30 head, 280 acres. It was very steep acreage; wonderful views though, and a south aspect so we were out on the land 2 weeks before everyone else in the spring. We had a Farmall C for our one tractor and that was enough; must have had 20 HP, so some of the comments as to how much horsepower you need fascinate me. Horsepower is overrated in tractors, but size and weight can be worthwhile. That said, 4WD is sure nice, and a roll bar is certainly worthwhile. I really like diesels compared with gasoline engines. At the dollar amount you want to spend you may be tinkering a lot of the time, but tractors are easy to work on as everything is out there for access. However, breakdowns seldom happen at a convenient time. Distances are so small in New England that you can go far and wide to find what you want, covering maybe 100 tractor dealers. NH has no sales tax by the way. As a teenager I logged with a small crawler, buying stumpage and selling logs throughout NH and VT, all the while taking no less than 12 college credits a semester so I would not be carrying a rifle for $34 per month, and so I now know a small crawler sure would be handy around your acreage. That crawler was gasoline, but today I would look for a diesel in the same or a similar model. There is a Mahindra dealer across the river from you in Gorham, NH, and that is not a bad area for you to look at used tractors.
