I have used both. Mowing about 5 acres regularly, sometimes assist with neighbors 7 acre pastures
An older model (early 80's) IH 234 2WD with a woods 72 inch mmm. Hated taking that thing off with a passion. At least a half hour off, and an hour to put the thing back on. It was a lower HP tractor, but it ran the mower OK, if you kept up on the mowing. If you let it wait an extra week or two, then mowing time doubled. The tractor ran like a dream, but was just a bit underpowered for the mower that was mounted on it. Basically used it as a lawn mower, occasionally pulled a ground drive spreader or a chain harrow with the machine.
Currently am mowing with a NH TC33 4WD and a Land Pride 72 inch 3 point finish mower. Can now mow in less than half the time, it looks better, and handles tougher conditions with ease. Connect and Disconnect in 5 min. The machine is quite a bit longer, with the front end loader, seems like a bus compared to the IH. Plenty of power to drive the mower. Love the FEL, and the utility that comes with it. The TC33 has enough traction to plow the private road in the winter (about 1.2 miles), as well a pull any implement I need.
For me, the larger tractor is a game changer. I spend less time preparing and mowing with the larger tractor, it is more useful around the farm. The MMM was easier to drive, and maneuver, but took much longer when looking at the total picture, especially when it came to maintenance. Had to replace the belt on the MMM once every couple years, have been using the current belt on the Land Pride for 3 years, and it looks like new. Do yourself a favor, get a CUT, with more HP than you think you need. Get the cab, 4WD, HST and a decent FEL. You will be happier for your choices. I have almost never heard anyone say, 'I bought too much tractor'.