I've got a Kubota 2350 4wd with a fel and an old Ferguson 35.
They both have their jobs around the house. The 35 gets used primarily for brush hogging. It used to be the do all tractor.
Wife bought me the used 2350 for father's day. I've had it about 2 weeks now and don't know how I ever lived without the fel.
It's smaller than the 35, but has a lot more oommf. The 35 has to downshift to now up our little hills, the 2350 never slows.
As for what you're doing, buy more tractor than you think you'll need. With your budget, I'd be looking at 50+ hp mahindra or a good used machine.