Good luck on whatever you decide spark. I think you would be happy with either one.
My experience is I went with a 26 hp tractor and was very happy with it. But mostly because I wanted it rather than need, I traded up to a 38hp (and I thought the dealer did me well on my trade since it was only 3 yrs old and he had it sold almost immediately). So for what it is worth sparky, if you can swing it, get what you really want. Unless your acreage is confined to small places where the smaller tractor will get about better, I can't see you ever being unhappy (other than the original cost) ever going with the larger one. Even the larger one is likely still going to be as manuverable or more than what you have been used to.
My wife always encourages me to get what I want. Because invariably when I do I am satisfied, and when I compromise there is always that little wish I did it different.
Edit: this is assuming they are both hydrostats. If the bigger one is gear, for utility work, I would definitely go with the hydrostat. Now if a person is doing heavy tillage and constant draft pulling, different story. But for homeowner use, nothing beats the utility of a 4wd hydrostat. That is not saying a gear 2wd will not work, because it will. But one is like driving a luxury car compared to driving a low end compact car. They both will get you there. It just all depends on how much you want to enjoy the ride.
