You were born too soon. If your birthdate was 1990 or later you would just start a "Gofundme" and ask the rest of us to pay for it.
There's only about a 60 lb difference, and the minimum recommendation for the 351 is only 17HP. If it meets your budget, I would go with the heavier winch. I've run Farmi's, both mine and my father's; I owned and worked the pee out of a Fransgard, and now have a UniForest35. They all are solid pieces of equipment, and I wouldn't hesitate to buy any of them. All things being equal though I would go with the Farmi or Fransgard.
I wish that I still had the 275, except in a little better condition than when I bought it in 2002. I ran the crap out of it and it kept on going, but eventually steel fatigues.

It was a great little tractor and I tried to find another; but there's no way that I will pay $10000 for a 30+ YO tractor.