I love to mow deep fields. So long as I know there are no stumps, cars, wads of barbed wire, or holes to fall into. My favorite height is eye level when seated in the operator station so about 6 feet tall. At that depth you're really accomplishing something and you see much more wildlife, though it is often chopped up. The eagles and coyotes seem to appreciate the lunch.
It is mowing season and I plan to spend all day on Saturday spinning the blades.
But yes, three or four times a year. If I wasn't trying to sell the woodlot, I could mow once per year and that would take care of all the trees and undesirable growth. The mowers can mow anything thinner than your wrist without slowing down.
This doesn't sound like Craftsman territory. Are you field mowing with the tractor?