I have a lot to mow including a high banked gravel drive about 1/4 mile long. I use my small 4 Wheel Drive Kabota tractor with a belly mower for a lot of the land. You can get heavy duty bush hogs for the wooded area also. However I have a Scag for the pretty cuts around the house. It's not a diesel like the Kabota but a beautiful cut. You might consider something that is a multi tasker since you have the other mowers already.
Scag and Kabota both orange country TENNESSEE Vols color.
We all are merely gleaners from the masters who were here before us.