Depending on the size of your pocket book, how much maintenance you're willing to do yourself, and how much of a kick you get out of being self sufficient, there are 100's of right choices and 100's of wrong ones.
I think most of the worng choices are in the category of too small (Garden Tractor) and too big (not manuverable enough for your terrain).
I think most of the right choices are in the 20-30 hp diesel CUT with live hydraulics, Cat 1 attach, and rear PTO.
Any 20-30 HP diesel from the big colors (Green, Blue, Red) and the imported big colors (Orange #1 and Orange #2) will work just fine with proper attachements. With all of these, the primary value is dealer support with fit and finish running a close second. High end on $$$, Low end on self maintenance, Low end on self sufficiency. If you go this route, I'd base my decision primarily on confience in the local dealer and much less on brand loyalty.
The second item to really consider is drivetrain. HST vs. Manual. If you want/need HST, then once again, dealer support is fundemental whether you buy an older used unit or a new one.
If you're a go it alone kinda self sufficiency type who doesn't care on the manual vs. HST front, then a Chinese crate tractor new can be had for about 40% the cost of the big colors. You will have to assemble it yourself, be 100% responsible for maintenance, and become your own tractor mechanic.
I took the plunge in the last category and have been having fun ever since, I mean working hard ever since.
My total investment so far for a 22hp 3-cyl diesel manual tractor with Johnny bucket, Kioti 60" RFM, Boom Pole, Wagon, 6"
Chipper, and BoxBlade is $9365 and 40 hours (3 weekends) of labor. A FEL would be another $2500.
When I was looking, I came real close to a Kioti LB1914, but for my limited use couldn't justify the cost. I looked at JD, but he was so bent on selling me $27,000 worth of tractor, that I completely wrote them off.
Marks (DIYGuy)
http://www.DIYQuest.com