It seems your driveway work, winter snow clearing and spring/summer maintenance, is your challenge. This is ground contact work, where tractor weight, 4-WD and loaded rear tires are most important. Horsepower is almost irrelevant.
You can always install tire chains for the winter. Some, who do not road their tractors, use tire chains year around in field work. High quality chains on those big rear wheels are amazing. Tractor tire chains come in steel and rubber.
What PTO powered implements do you foresee operating?
Beginning at 80-horsepower tractors are equipped with a Category III Three Point Hitch. I would stay with Category II equipment which is readily available and competitively priced. When you get to Category III implements it is a relatively small pond and implement prices escalate.
My tractor is Category I. I like being able to order implements from the internet, often from
everythingattachments.com or
Iowa Farm Equipment.com, and have said implements arrive on a semi trailer three or four days later. Almost all Category I implements are available in Category II from the same venders. Not so, Category III implements.
As you described land conditions as very hilly, the MF 247 almost certainly has loaded rear tires.