The first thing is to decide whether you want to work with your land, and improve it gradually with trails, etc. or whether you want to "dominate" it, and eliminate all the brush, etc. in a short time. I have enjoyed working with my land immensely. I putter along, and keep an eye on how the things I do affect the wild life there, etc. It will take some doing to manicure that much land. Don't forget that what we view as brush, and briers is heaven to rabbits, and other small game / birds that we also enjoy having around so I would leave at least some pockets, perhaps near water, and just kind of enjoy what happens there as the normal cycle of change takes place. For that much land you will want some hp, and weight. I would look at the Kioti DK series like Islandtractor's DK45, the Kubota grand L, or MX series, the JD 4105, or perhaps the fancier equivalant, Massey's, etc.
I went the opposite way with something small enough to fit between all my boulder obstacles, etc., but I am working on a miniature scale of your land too. With no weight I have to be careful, and have fewer options, but my trails have to be very narrow in places because of VW sized rocks, etc.