Kodiak,
Very well thought-out rationale, obviously worked out in all that seat time you must get! My situation is slightly different from SethO's. I am buying an 18 acre part of a former dairy farm with a 100' of "po' man's" waterfront on Lake Ontatio - (a bit shallow and weedy but you can launch a boat). I am fortunate in having a well-maintained classic post & beam dairy barn, 36' x 60' that will provide garaging for vehicles and tractor, as well as workshop. I may have to add a pole barn ell or machine shed for implements. My wife tells people we're buying a great barn on 18 acres that also has a house . . .
The land is mostly scrub and open pasture on clay - the 18 acres were the barn-yard and pasture for the cows; hay and crops were brought in from nearby. So to do anything with the land some renovation is in order. My wife is talking a large pumpkin patch and maybe Christmas tees - both pick/cut your own, on a small scale. Maybe a couple of acres of pumpkins and 500 Xmas trees. I will use our Simplicity 12.5 LTH lawn tractor for finish mowing and snowblowing walkways if I can find a snowblower to mount. So tractor uses will include some field work, landscaping/rock work, snow removal for 100'+ drive with fully adjustable back blade, spraying, brush-hogging trails for planned dogsledding with Chinooks (hybrid pulling breed - great dogs!), putting in/pulling out a seasonal dock, and future lakeside cabin construction. The emerging philosophy I am seeing here is - get real! Buy appropriate size for most common and needed tasks, rent/beg/borrow/?steal? for one-time or unusual projects. In my case that could include initial plowing/disking of pumpkin field (I grew up on a northern Wisconsin dairy farm on clay; that can be unforgiving soil) and excavating for cabin construx etc. And even though my wife is saying "You want a backhoe, right?" I still have to pay for it sooner or later! I do not at this time see a reason to trailer anywhere; my current road rig is a Toyota Tundra 4WD V8 rated to pull about 5K lbs.
BTW Kodiak, I am new to NH. Is the TC33D in the same class you are describing? Do you think it would be a good fit for what I am describing?