I'm going to dive in here also. My situation is similar to yours, just a bit smaller. I have a 52 acre wood lot, drive way is about 200-250 feet, I heat with a outdoor wood burner with oil backup. I am also looking for a machine to plow snow and skid a few logs, and haul firewood.
I currently have a JD 850 (22 hp, 2wd, gear, no FEL) I can ALMOST do everything I need to do with it. Size does matter /forums/images/graemlins/grin.gif I am currently trying to make up my mind between the JD 790, and the 990, both with FEL's. The 790 in 30hp (16K after taxes) and the 990 is 40 (22K after taxes). One reason I am going gear, is there is less stuff to break /forums/images/graemlins/laugh.gif less buttons to push, and I dont need the bells and whistles. I am tending toward the 790 simply because of total machine size. Would the extra 10 hp be nice? Maybe, maybe not.
Your, and my biggest problem is getting around in the woods. If you go into a tree farm, you really have to watch what you are tearing up, that is income and as a tree farm there is a 5 year inspection so you can keep your farm status.
I have run a (fathers) 27 hp JD 950 with a hoe, 5' brush hog, FEL, 6 ft sicyle bar mower, 2 place tedder, and hay rake. I have put a carryall, a single bottom plow, and a 6' back blade behind my 850. I put up 29 cord last year with the 850 and a carry all, and moved it from pile to furnace all winter. Admittedly I had it loaded to where the front tire to ground contact was pretty questionable at times, but that was me, not the tractor. With a FEL the weight will be more distributed. A friend at work has a 790 and pulls a 5' tiller without a problem.
I have skidded logs with both, no you cant take 5, 24 inch trees behind you and walk out through the woods, but you aren't a logging operation either. You are going to pull tops if you get it logged, or a dead, blow down, or cull tree when you get firewood. You can drag them out and cut them near the pile, or cut them in place and put them on the carry all. Cutting in place seems to work better for me.
3 more reccomendations. Get 2 saws a big one and a little one. I have a Husqvarna 359 and 136. The big saw is great for tree reduction, the little one is for limbing and for when I get the big one stuck /forums/images/graemlins/shocked.gif . I made 2 holders for my carryall to hold the saws when I head for the woods. Also a cant hook, or a peavy is a MUST when cutting a lot of wood. Buy the saw chaps also, 54 bucks vs a leg is a good investment.