Thanks for the input! It would seem I'm not so nuts after all
To answer a few questions...food plots/prairie areas are out of the question. The area I mow more or less requires it as I have the house (which sits back off the road a ways..i.e. big front yard), a 3-car detached garage, so have to mow around it and the area between it and the house and then behind that a 12,000 sq ft barn which needs mowed around. Also have to mow areas along the property on the other side of the driveway and along the main road.
I use my tractor and 7' cutter for the 10ish acres of field behind the barn
The yard is rough because when the home was originally built (in 1900) no yard work was really done...they just more or less kept mowing the field grass/weeds until grass sort of took over. From a distance, it looks ok, but it's rough from rough ground, grass clumps (I'm convinced I have every known type of grass growing in my yard in one place or another), holes, and weeds. Honestly, I don't care about the various weeds. I'd go bankrupt trying to keep them at bay...and the dandelions every year just take over everything. Even if i could rid the yard of those, none of the neighbors bother so in a year or two I'd be covered in them again.
I'm perfectly happy with having a less than stellar lawn in terms of what is growing in it, I'm happy to just mow it, but I hate the roughness (which is primarily due to the ground itself). I don't care about keeping any of the current stuff alive if I tear it up. I'll go in sections and plant new seed as I go.
In addition to generally rough ground I have a lot of humps/hills/depressions that need smoothed. I have a Mahindra 5035 and a 7' box blade now. It sounds like the Harley Rake may be the way to go instead of a tiller. My soil is mostly clay and we have lots of rocks, mostly small (softball size or smaller, mostly smaller).
I like the Ferris ZT with suspension, but that bad boy is a bit over my budget and way more than I want to spend on a mower. My current pick is the BadBoy Outlaw XP, 72" deck and the 36 HP Vanguard engine. $9,400 (which is more than I ever imagined I'd spend on a mower) is a fair chunk less than what an equivalent Ferris costs (or Hustler, or any of the other big name mowers). I could get a smaller mower in one of the other brands, but then I'd kind of be defeating the purpose.