I've never intended to skid logs with the skidsteer; only load, push tops around, process firewood, level roads, fill fallen tree divots, post hole auger, snowblow, and whatever else needs doing. A tractor can do all of that, but the FEL on a compact tractor with the same size of a skidsteer wouldn't be able to lift much more than my electric winch on the log arch now. They also don't have the turning radius or breakout force.
Plowing snow is cheaper, but has limitations. I could've paid for the machine this winter if I had a snowblower on one. With plowing you have to have somewhere to shove the snow, with blowing it you just have to have somewhere to aim. As the snow builds up along the sides of a road/driveway you encounter more and more resistance to pushing it off the side. Snowblowers don't have that problem. You can also go right up to a garage door with a snowblower, with a plow you have to raise the plow over the snow and then drop it down by the door and pull back to then shove it off to the side. In my neighborhood, there's several tuck-under garages so you can't plow them out efficiently anyway.
Snowblower on a tractor requires driving in reverse - not something I want to do for miles at a time.
Looked up the 440 skidder again to be sure it's what I thought you were talking about. That size machine is exactly what I don't want in my woods. I can pull 20" 16' long red oak with my atv and you'd never know I was there afterwards.
Never thought of skidding logs with a skid steer. They don't work well in areas with soft holes, soft dirt, off kilter terrain and such. They also are terrible to maintain (everything crammed into the tub) and lousy visibility which is a BIG deal in the woods. Then you say a skidder is to big but skid steers tear up everything. Skid steers were designed to load and scrape level barns and barn lots of manure. Work ok loading gravel and several other task on level lots with at least a gravel base. Terrible any where else. Their popularity steems from there portability and they will do many jobs , but many half a$$ed. A multi terrain loader works so much better off road, especially leveling out dirt where the skid steer is a poor choice. Around here unless they are working on concrete skid steers are not sold any more for contractors, and light construction. The rubber tracked machines make earth moving and grading child's play due to the lack of pitching movement so inherent with skid steers. Many use the for snow removal just fine to. You realize there is a difference between multi terrain loaders and compact track loaders? The MTL have torsion mounted boggy wheels that follow the ground instead of the solid track frame of the CTL. Still a 60 hp tractor will be far more versitile and stable.
As far as blowing snow with a skid steer , you know you need a very expensive high flow pump added on?
You can buy a much larger tractor compared to a skid steer. Gear drive instead of chain drive. More traction. Won't tear up the land as much and more stable, better visabilty, better maintenance ease, better support in most areas(mechs hate skid steers). You don't have to have a rear mounted snow blower. Modern tractors can drop the loader in 2 or 3 mins, some now without leaving the seat. A front mount snow blower has a sub frame that goes back to the draw bar. As long as everything is on a level solid surface you drive over the drawbar until it slips on the drawbar. Drop your drawbar pin, hook up you PTO shaft and hydraulic clyinder hose, depending on model there might be two pins in the front but most have a drive into pins now. Five for the best and fifteen for the worst and now you have a much more efficient PTO powered blower instead of a hydraulic blower on the front of a pitching bronco.
A 50 -60 hp 4wd tractor while not as ideal as a skidder or fowarder is much better for the task your asking.
So you asked the question of are you nuts. The answer is yes because you ask questions but don't listen to everyone's advise. If you already owned one and money was tight, ok. But when you are going to buy one and still don't listen. Well it sounds like you won't listen to reason so I will step away from the wall I am beating my head against.
Think of me when you just ran over a stump or rock that you couldn't see and your laying on the side and your head hurts from flailing around in the cage!