Thanks for the well thought out response.
A skidding winch is probably going to be a not-to-distant purchase following the tractor, as it's realistically the only way I can see to access a lot of the land. I will be able to cut out a bunch of small stuff to make main thoroughfares for the tractor, but I think I will basically be constrained to staying on those paths, as everywhere else is so rocky and uneven.
I'm still not sure on how much hp I really need for a PTO driven rear blower. Maybe I need to post specifically in the snow removal section? I know the rule of thumb is 5 Hp per foot width, but that doesn't really tell me how much quicker I can expect to move snow versus my current Ariens 28 deluxe walk behind.
From multiple responses here it sounds like maybe I should rethink the idea of getting a grapple. I initially thought I'd use it for harvesting rocks, building retaining walls, and loading firewood into bins, but prevailing opinions seem to be that the grapple probably won't work for loading firewood into bins, and I can probably transport rocks easier with a sled, while using straps off the loader to place them on a wall. As you mentioned, skidding rocks on a hood isn't a bad idea either.
I hesitate at buying a JD or Kubota solely because of the lesser "value" due to the higher price. However, again, prevailing opinion seems to be that there are other considerations that might likely outweigh that hangup. In JD and Kubota, I'm guessing I would probably be looking at either JD 3039R, or
L3560, both with a cab. Really, as I get closer to the purchase (January or so time frame, I'm hoping) I think I just need to get out and sit on a bunch of them as well to also factor in ergonomics.