rtimgray. . . I will first say I am biased toward HST transmission tractors because they are easier to use, easier to learn how to use, and because, especially for a new user, they are safer. I play with antique iron as often as possible and like to restore it, but for my tractors that I acutally use, I pony up the extra money for HST. I can use either, but HST is also the standard type of transmission on many industrial machines, and it is faster to use with a loader and faster to use with a mower if there are lots or twists, turns and trees to deal with. All that said, I am not trying to stir up a Gear vs HST debate. I will easily and quickly admit that any gear tractor can do anything a HST tractor can do, and gear machines are better suited for pulling a plow too. We have a newbie looking for help, and the newbie has a grade to deal with, on hills HST is safer for both experienced and new users.
Friar Tuck, With 16 acres there is going to be plenty of stuff to work, my thought was that a 33 to 35hp tractor would have the PTO hp to handle an 84" finish mower deck, a 72" rotary cutter, a 72" snow blower and a host of other implements. The TC33 or DX33 I previously recommended is built on a slightly smaller frame than the TC35 / DX35 which may be an advantage IF the property Friar Tuck has includes some tight spaces, otherwise either is fine. Any equivalent brand in that size machine would do the job. I just don't know exactly which size JD or Kubota, etc is comparable to a TC35 / DX35 and still offers a HST transmission (but I know both brands do), I do know that in that class of machine (above 33 to 40hp) only NH & Case Farmall offers the curved loader arms, these machines, as well as JD & Kubota also feature flip up PTO shields, extendable lower links, and cushy seats on most machines in that class.
I see you have added that you are in Illinois, since you have a grade to deal with I'd have to guess you are in the western part of the state, and since you have snow, I'd say maybe Galena area or perhaps somewhere roughly in that general quadrant of the state??? Not a lot of snow over there, but if you are up closer to the Wisconsin line you can get a dumping on in the winter. Anyway, a 60" blower would also do the trick, but you'd end up making one more pass on the driveway to clear it. That might not be a big deal for you.
Your best bet really is going to be to go out and shop at all the local dealerships, we have several people here from Illinois, if you post what city you are near, someone may be able to direct you to a couple of local dealers who are good dealers.