Look for something in the 30-45 hp (pto hp) range with 4WD, power steering, hydrostatic tranny, FEL with 6-ft wide bucket and at least 2000 lb lift capacity, ag tires, chain hooks on the FEL bucket, skid steer attachment on the FEL so you can change quickly from the bucket to the snow plow, double or triple rear hydraulic remotes, possibly one or two front hydraulic remotes, a heated cab for those VT winters. Since there are hilly sections on your property, check the maximum track width adjustment on the rear wheels (you want the largest width you can find for stability).