#3...need 4x4? Maybe not. Want 4x4? Absolutely. The land is pretty darn hilly.
I see listing for tractors labeled as 4wd and MFWD, and I'm not sure what the difference is. As far as I can tell on the "shuttle shift," it appears to be a manual tranny with no clutch? Hydrostat would be preferred...as well as 40hp+ (35-40hp minimum) to pull a bigger bushhog (6'). We'd probably keep the tractor a looong time, and I wouldn't want to have buyer's remorse in a year or two. We probably would plow up some of the land, but not much right now. Also, looking at tractors with a loader.