Your equipment 'stable' is impressive. I need to either fish or cut bait: spring for zero(s) or get someone with big guns to help out. Either way, it is going to be costly. Some sections here need to be done twice a week because they get high nitrogen run-off from the cattle pasture up the hill, even though there are no more cattle - but that is another story....
Good luck with your leaves. I still have lots to fall and be cleared, but they're all under snow, as of last night, so I can ignore them for the time being.
I have some “tricky” spots, but there is a lot of room to just ‘let ‘er run’! The only thing is if you hit ruts ... we had some trees taken down & the guys dumped the chips ‘on us’. The big chip dump truck got stuck in the field & there are some ruts - you hit them at speed & you feel like you’re losing your kidneys! Some young cousins also got a 4-wheeler out there last Thanksgiving when it was waaay too wet - they loved almost getting stuck & spraying mud everywhere, but I have their ruts to contend with as well.
Look around for a non $$JD$$ zero turn. My brother’s is yellow - not sure of the brand, but it does great for him. It cut his mowing time in half when he went from ‘tractor’ to zero turn. Being able to make short turns (just whip around to go back the way you came) instead of fighting a steering wheel saves a lot of time/wear & tear on the driver. The added bonus is they’re fun to drive, once you get used to them. When I got my first one, I would take it out in the fields first & warm up on the steering before mowing in tighter areas, like the yard.
I still laugh at my brother - when he got his first one, it was delivered & sitting in the driveway when he got home from work. His wife & (grown) daughter were outside & the daughter got video .... he jumped out of his truck, still in his coat from work, jumped on the zero & took off .... right over my SIL’s flower pots ... very embarrassing. I saw him later that evening, out in the field, working on getting used to steering, going around trees, etc (he had the mower running, so he actually did some cutting for me). You need some space when you’re first dialing in the steering :-)