In the FWIW department, I'll toss out my experience with my 2310 over the past 15+ months (< 100 hours).
My dealer mounted a single hook on my bucket at no charge as part of the deal. I have found it to be very handy. Not sure if 2 hooks would really be an advantage for my use.
I have the R4 tires and like them because they don't dig up the lawn. They worked fine last winter without chains and have been great in the woods. I would probably be just as happy with turf tires, but don't regret my decision. Then again, if I had the opportunity to pick up a deal on another set of turf tires and rims, i would probably do so.
My tires are not filled, and it hasn't been an issue. As small as these tires are, I think it adds < 200 # total, so I'm not sure how much of a performance issue that makes. I usually have either the BH or snow blower on the rear, so there is good balance.
Mine came with a block heater, which I have used a couple times. My tractor is in an insulated but unheated garage that is attached to our house. It gets pretty cold, but not like leaving it outdoors. OTOH, because the tractor is in the garage, my car stays outside (wife's car is in the other garage bay....). Remedy there is a 3 or 4 bay garage.
I don't have the service manual yet. It's on my list, and maybe I'll give the dealer a call tomorrow. I have the manuals for all our other vehicles and will get one for the tractor, too.
Every once and a while I see an oil/grease drip on the floor. Usually from the rear after I have changed implements. It's only been a couple of drops and nothing I worried about. It hasn't leaked any other fluids from any other places.
Auxiliary ROPS lights are a must. I put on 4 (2 front; 2 rear) before last winter. It was pretty easy to add another switch to the dash and wire in the lights - and they are wonderful. By comparison, the ones that come on the tractor are just a notch above useless. I got mine at Tractor Supply, which is also where I got the waterproof switch.
I was concerned that having an extra set of lights on the sides of the ROPS would be a recipe for disaster when I went into the woods - but so far, so good. Haven't broken them yet (and hope I don't regret making that comment).
Our property sounds much like yours - and I am very pleased with our decision to buy the Massey. My only regret is that between lousy weather and work, I haven't had more time to use it.
Good luck!
Jay