We mow 15 acres of high grass twice a summer with a Massey Ferguson 1533 - 33hp - and a 60" bush hog. Working in the Blue Ridge mountains of southwest Virginia where the temps are usually in the mid 80F... it has never overheated because of 2 things: cleaning the screen when the temp is seen rising, and slowing the travel speed for the same reason. We mow hills - some quite steep. Slow is the key. 15 acres at the fastest pace I ever took takes about 10 hours. With high thick grass, it takes 14-16 hours on the hills - largely owing to operator fatigue. When we get tired, we change operators or end the day.
Non Cab tractor - gear driven - operated in 4w drive the whole way - get out the sunscreen and good hat!
Never had a problem using the machine for trail work. Owing to the intermittent duty, it does not heat up. Besides, on the trails, we are cutting thicker brush and not grass. Property is 200+ acres if mostly wooded land. We are building trails to allow access to the inner parts of the "woods".
Our 2005 Massey Ferguson is a baby.. has only 300 hours on her. She sat for the better part of 10 years... We have put 200 hours on her in 2 years. Still not big use.
I don't feel a 6' mower would work on this tractor. The hills drop the RPM now. With a bigger mower, I think they would drop further and would strain the machine. Our dealer felt the 5' was the right size for our machine.