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I had a Bobcat 48" hydro WB that I would do all of that with...1st pic would probably be sideways due to the possibility of hitting cars if you slid down in wet cond..although it looks to flatten out the further away you go.
2 pic looks uneven at the corner of the fence...the hill on the far end with the tel pole looks really steep...so maybe not that. Do you have any local friends to borrow and try? Are you already looking at anything in particular?
I know this is going to sound crazy but it really works well. Keeps the operator safe to.
I used to mow steep retainment walls around large petroleum storage tanks for a pipeline. We used modified 21" push mowers. We removed the handles, put eyebolts the front and rear corners opposite the discharge side. Hooked rope to the eyes. Walked back and forth across the top of the wall. Just let a bit more rope out to move the mower down the hill for the next pass.