Thank you all for your responses!
I had pretty much convinced myself this was the tractor for us but now I am not so sure. I'm not sure that it isn't but I am going to follow the advice above and go to the dealer with the wife and drive both the 1025r and the 2032r they have there. Leaning towards passing on the backhoe as well, but not completely sure about that either. The ground clearance issue is, frankly, one I hadn't really thought of, thanks to all that pointed that out.
So... about the property: It was a horse farm but we aren't going to have horses, we're looking at sheep so the pastures will be grazed and we will have some needs as far as moving hay & water. Although the property is 15 acres, there are probably only 4-5 acres that are pastures and will need to be bush hogged. There are woods, a creek, the house & lawn, and buildings on the rest. One of those buildings is a covered riding arena. There is also an outdoor arena. Though we don't have horses, we do ride in the arenas and it would be nice to be able to drag them. Some pictures:
The furthest, highest (growth wise) pasture:
The riding arenas: