Look again at how many of us have more than one tractor. It's not just because we are fanatics, there's good reasons to have several. And with 58 acres, I believe it's just a matter of time before you'll be joining the multi-tractor club right along with us.
So maybe it doesn't matter whether you start first with the big tractor or the smaller sized one ..... or for that matter whether you start with new vs low hr used.
Just be sure that it has a 4wd, a loader, and a back blade. Most brands will do you just fine.
Enjoy,
rScotty