This is a well organized post. All the important information in the question, and nice helpful answers in reply. boy it is so good it is almost boring. So to juice things up a bit, I will play the role of the reckless lunatic and offer some hair brained solutions to your land management challenge (just for fun)
1) Spend far less up front on a collection of antique tractors, garden tractors, and implements. In addition to placing your life at risk on the slopes, all your free time and money will be dedicated to endless repairs. Plus, the leaking oil and gas will keep the weeds down. Been there done that
2) Buy an off brand compact tractor at a farm store, used car lot, or flea market. You will save a bundle initially, and your land will return to 'ever wild' status while you wait for more faulty parts every other month as it breaks down.
3)Do like my neighbor and buy a $1500 lawn tractor and flog it to death over the pasture each week, clanging and banging until it blows up.
There. Now we got something to argue about /forums/images/graemlins/blush.gif