I had 40 acres in the Santa Cruz Mountains in California and all but a bit of it was up and down, some of it pretty hairy indeed. I had a Kubota B21 and used it for years with only a few scary moments. That said, I ALWAYS understood that my wheeled CUT, with the standard teeter-totter front end was pretty much like a tricycle and required that the rear tires remain on the ground at all times for stability. Yes, rear wheel spacing does make it more stable, but it will not cure the design "problem" with most wheeled tractors and their front axles.NEVER try to work or even travel across a slope of any steepness. NEVER try to raise your loader above the axle height to dump it when your are even diagonal to a slope - that was one of my scary moments when doing some road work, I was pointing down hill on the road maybe 30 degrees cross-slope when I tried to dump a bucket load over a barbed wire fence into a canyon - the right rear tire lifted off the road and the tractor started to roll towards the downhill; only quick action putting the bucket down, crushing the barbed wire fence, saved me from dumping the tractor on its side.If I would have had the money, a better option for my terrain would have been a track-steer for sure. But, they don't have a TPH or a rear PTO, of course. I like the PowerTrac idea and it's CG is certainly lower but you know if it will or will not work for you. These articulating CUTs might offer better stability but I know nothing about them other than they have good engines and an interesting design. Certainly would have been in my consideration on my mountain, if the price was okay.
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I have an 886 I love as a chore and hay tractor. It might be bigger than you want but you mentioned the 86 series. It has a dry clutch that is assisted. You can push it in or have it hold when the time is off, it's just harder. It does have wet brakes and full hydrostatic steering. Those go away with no engine, but a diesel isn't likely to stall for the reason you had with yours. They usually run badly before a filter is plugged enough to shut her down. I use an old Farmall M for grinding feed. It has mechanical brakes. I wouldn't want to trust them on hilly anything with something behind me. I've never seen mechanical brakes that were as good as hydraulic. They may be out there, but they aren't on this farm.
I just mowed, raked, and baled a new property - one time thing for surveyers. It was white knuckle steep. The kind where you have to brace yourself in the cab to stay in the seat. I have the tires on the 886 set wide and filled. Even with the cab on it the center of gravity vertically is 40 inches so it is below me a ways. Check with the Nebraska tests to find out the center of gravity on one you are considering.
I'm a red guy at heart but run green for tillage. I like both. Just find one that makes you comfortable, set it wide and weight it down so you don't lose traction.
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