for 5 acres, i would want something in the 27 to 35 hp range.
You think you only want it for X, but you'll want it for Y and Z, and something bigger than a SCUT is way mroe useful for almost exactly the same money.
My neighbor has 5 acres and a 20hp JD (I dunno the model number, JD model numbers make no sense to me) and he struggles. He put too big of stuff on it (his fault, not tractors) and it's beating itself to death. It probably won't make 1000 hours and it shoudl easily make 3 to 4000 hours. (of course, he's an idiot, so take that with some advice)
However, the tractor is SLOW, the FEL is SLOW and it's not nearly big enough to do many things. (PHD? got fences, you'll want that, i use mine a ton, tiller/ripper, you can get small ones, but on 5 acres they just disappear and tillers wiegh a ton).
For 5 acres, about 30hp seems about right
4wd (you never know, mud, snow, etc, and 2wd and FEL work can be frustrating)
Nearest dealers? you should exclude any of the ones that aren't near and/or you don't like. Dealer support is key.
Have you thought about Massey Fergeson (AGCO, same thing)? Their 1500 series is cheaper than the equivilent JD.
Also, the NH boomer TC tractors are pretty sweet.