Bama, I was in a similar situation before I bought my first tractor. Had 16 acres with a couple of acres worth of mowing, long gravel driveway to maintain. All told, I spent about $6K on my (newly refurbed) Yanmar 2210, a bush hog, a box blade, and an older riding mower. That setup worked really well for me. I added another 45 acres the following year, but it was mostly woods. In addition to the rough cutting and box blading, the Yanmar helped cut a lot of trails, moved a lot of dirt (bought a 3pt dirt scoop eventually).
I got a LOT of stuff done with that 2wd Yanmar, and still use it. They are excellent, reliable, simple machines, with good aftermarket support.