I used to cut the grass myself with a walk-behind mower but gave that up when I turned 75, thing was always a PITA to get started even with priming it properly, although I didn't really mind the mowing per se.
But this guy has a few different sized tractor mowers,, so he just brings what he figures he can use most easily. My place has PITA areas to mow around, but my other land that adjoins it is much more open, so sometimes he brings two machines to make very short work of that second place.
All told what he mows is probably 3/4 of an acre, most of my several acre total is out back of some stone walls on a gentle rise towards a steep ridge that is behind another set of stone walls and runs into the woods where deer, coyotes and the occasional fisher cat, weasel or bear hangs out.
I just get the meadow area bush hogged every few years to keep the trash trees down and otherwise let it be a little preserve for edge habitat birds, foxes, rabbits, assorted other wildlife (weasels, skunks, possums, frogs, a few species of mostly harmless snakes) and yeah, woodchucks. Well their babies are cute... for awhile. I let them be, since I don't have horses out there that could break a leg stepping in their damn holes, and I know to look out for them on my infrequent forays after greens, grapes, berries or rhubarb.
My sister's father in law who used to own the place next door said the reason for woodchuck holes was to have some place to put all the baseball sized stones that would get heaved up by frost and thaw action over winter out in your veggie garden.

He said that during the first summer I had this place. I was sure he was kidding. Then in due course along came spring. The rocks heaved up were a revelation.
I used to mow a strip up into the meadow and then mow a square to make a nice little place for a picnic lunch with pals. We're all more or less fit but still we have grown somewhat fearful of falling on uneven ground now, so those days are pretty much over and the picnics happen right in the backyard proper!