That property would be perfect for me! lol I had to fence in my pasture by hand, slamming in Tpost with one of those fence pounder thingy ma bobs in June of last year, it was hot and miserable but on with the story.
It all depends on what you want to do with your property, in my experience a 445 or 455 will do just fine. Find one that's a 99 or 2000 with under 1000 hours that's been taken care of, $1500-$3500 and you shouldn't have too much trouble with it. My dad has a 445 he bought new in 2000 and we shared it for 2 years when I bought my house before I could buy one. I used it for stretching chainlink fence, cutting grass ext, he had the wide tires on his and the deff lock works wonders. I moved around a 1500lb trailer with it many times, used it for yard work ext, it handled all I needed and some, I had 3 head of cattle at that point.
The only reason I got a tractor was for feeding the cattle, I'm 26 and I knew if I had to handle square bales eventually I would wear myself out so now I feed with round bales, that dramatically reduced my labor feeding the cattle (I kept mine year around).
So back to what I would do in your situation, with your land and all the projects you could plan todo a tractor would be very useful BUT you can easily get by with a old 445 or 455 with a bit more physical labor from yourself.
If I had your place I would fix the fence first, make sure it's able to hold in livestock and I would buy 3-4 head of cattle and let them loose, they will keep the grass ate down and gain weight off it, late in the fall sell the cattle or butcher them, buy 400-500lb weaned calves in the spring and sell in the fall. With the cattle eating the grass in that section your left with under 2 acres to mow, a garden tractor won't sweat on that.
Most fence can be repaired by hand, stretched with a come along or garden tractor ext.
Cattle are easy to take care of, they don't really need shelter, they need some shade, fresh water and plenty of grass to eat, I didn't know anything about cattle, found a steer CL for cheap and brought him home, I had maybe 1/4 acre pasture fenced in, I fenced in by hand another acre and have 3 head but I have to supplement with hay sometimes due to lack of pasture. You won't need to supplement with 4-5 acres of pasture fenced in. Generally 1-2 acres per head of cattle.
As for transporting cattle, that can be done with a stock trailer or old 2 horse trailer, most sell for around $1500 but I have seen them needing work around $600, I have yet to buy one so I just use my dads 4x6 single axle trailer with a horse stall rubber mat on the deck, it will carry a 1100lb animal safely (1500lb axle) but I have a risk of them jumping out, I have bought 4 cattle total and hauled one to the butcher this way already and so far no probs, I halter there heads down so there not tempted to try to jump.
I also have chickens, super easy to take care of also.
I'm just south of Columbus Ohio, I would be willing to rent your pasture for a season and bring my tractor out to mend fence or whatever the pasture needs.
Another option is like another guy said is let the grass grow and let a local guy cut it for hay, not many guys would fool with 4-5 acres but a local guy that can drive the equipment over would. You will get paid something and not have to mow the pasture.
