skim read the thread.
the lake, uneven / hilliness of property, and woods, is the big concern stuff.
skidding out trees that you have dropped, is about only thing that is going to push you, for wanting a bigger tractor. bigger tractor being 4wd, MFWD, or like, more weight (weight is king in tractor stuff majorty of the time (more the better)), more lifting capacity, larger engine.
due to you tasks most likely involved, will be a lot of forward/backward motion along with changing of speeds, a HST (hydro-static transmission) most likely better for you, and all the multi tasks.
FEL, most likely a requirement for you, and not optional,
going to suggest a TNT (top and tilt) setup for your tractor, at bare min, replacing the top link on 3pt hitch with a hydraulic cylinder. if you have spare cash, then maybe also replacing 1 or both side links on the 3pt hitch with a hydraulic cylinder.
2 rear hyd remotes min, 3, if you go with both top link and 1 or 2 side links for a TNT setup. this should give you enough for what ever 3pt hitch attachment you end up getting / using.
check chains / sway chains, swinging draw bar, for 3pt area of tractor, most likely an other requirement and not optional for you. for various tasks the tractor will see.
left/right rear steering brakes (separate pedals for left/right rear wheels) = a requirement, and be on opposite foot than the gas/hst pedal/s a lot of maneuvering and FEL work, and may be only way to keep the machine under control and be able to steer the machine.
with woods, there is a good chance you may get a "12v electrical winch" for tractor. in that case, if they give an option for a bigger "alternator" get it.
for extra weight, and help stabilize the tractor hills, fill rear tires with a fluid, then double check manual to see if recommends filling front tires or not ((it differs from every make/model out there))
if the rims allow for it, have tires swapped around, to obtain a "wider stance" for the tractor. for extra stability on hills.
having a differential lock (able to lock rear tires together), can be nice getting your rear unstuck at times. not a requirement but nice to have, 4WD, and FEL, and split rear brakes, goes a long ways, but at times, it is easier to tap the differential lock. and up and out of the mud hopefully.
if you have an option for "power revers-er" for the transmission, same speed forward/backward. it can be a nice thing to have, have ran backwards a lot (less time vs turning around a couple times, to do what i am doing on longer runs)
3pt hitch, quick attack, pats easy hitch, telescopic lower lift arms, get one of them, i am favor of telescopic lower lift arms. the other two puts things a few inches further out behind tractor, and reduces over all lift capacity of the 3pt hitch.
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a lot of above is tractor specific stuff, that can be cheaper bought up front and at same time as tractor. vs saving and DIY or paying someone later down the road to add to tractor.
the one thing i did not mention was a 3pt hitch backhoe with a sub frame. this tends to be a high ticket item. if you want one, get it at same time as tractor, you more likely get a bigger discount this way. backhoes are nice for trenching, stump removal, ((biggest things seen here on TBN)), but have used mine to get myself unstuck, loading odd objects into back of a pickup truck vs using FEL, carrying some extra dirt in backhoe bucket and in FEL. ((needing to drive clear across property from were i am getting dirt, and needing to place it)). putting in metal T posts, removing old fence posts. and few other things i done already forgot about.
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my guess something in the 25HP to 35HP range for tractor engine size, make sure tractor is not an over size riding lawn mower... there is a grayish line between, riding lawn mower frame, vs a larger heavier frame, and more ground clearance under tractor. you will want the bigger heavier frame most likely. due to mud/snow, and everything the tractor will most likely be seeing.
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i realize you are wanting tractor specific info. and crunching it down to final choices... but this is more food for thought, and making sure you have things covered, and understand various compromises, you will most likely make, in getting something you want / need for your property.
, if price was no concern and ultimate feedback on the 4000 series as good as the advertising, then a 4000R probably where I would go but sadly the price hard to justify for basically property maintenance/recovery and maybe some hobby 'farming', however the internal debate still raging so all the feedback really welcome