Most Skid Steers have smaller wheels and tires than most tractors. The larger wheels and tires on most tractors bridge holes, burrows and ruts better than smaller Skid Steer wheels and tires. Larger wheels and tires permit faster ground speed and less operator disturbance.
"All Terrain" Skid Steers do exist. No Skid Steer that I know of has a Three Point Hitch, for good reasons. A tractor is the right machine.
In my hot/humid Florida experience cleared and graded land settles for several years as buried branches, roots, etc. decay. The settling should be fairly minor. But I do not know your situation.
You can smooth fifty acres really, really smooth but it would be a big job. Full time hay farmers around me use large rollers to create smooth conditions so tractor passes can be made a six (+/-) miles per hour. These smooth fields are in hay every year, hopefully three hay crops per annum. Smooth fields reduce costs.
The only suspension on tractors and Skid Steers is the air in the tires. Turf tires might give you a slightly softer ride on your tractor; especially low inflation pressure radial turf tires. You would need to buy new rims to go with turf tires.