Lots of great comments! I would add that it depends somewhat on what you can find used in your area, and how much you want to spend. Most older tractors take at least some tinkering fairly often, so if you are not mechanically inclined or willing to do the tinkering, plan on buying a newer tractor and paying the dealer to fix it.
My criticism of most of the newer tractors I have seen is that lots of the outer parts are plastic or some kind of composite. I would be worried about damaging them and not that many years down the road not being able to replace them. Most tin can be pounded back into shape if it gets dented, or welded on if it rusts out. Not so with plastic. Newer tractors are also often very complicated, as compared to the old beasts. I would expect lots of wiring and component problems with recent tractors some time in the future.
I would look for a good running tractor that is equipped with a decent loader. Most of my experience is with Fords, and there are 2 New Holland (with Ford) dealers within driving range, so I would probably try to stick with Fords. Gas or diesel? My experience is that my diesel tractor uses about half as much fuel to do a job as my slightly larger gas tractor. But to get the diesel to start in the winter, it must be plugged in for an hour or two. The gas tractor will start without heating. 4 wheel drive? Nice to have, but not really necessary for the jobs you mentioned. A 2wd tractor is a bunch simpler, but they sure can get stuck in deep mud or snow. For plowing snow, a 2wd will work fine if you have good REAL tractor chains. Power steering is nice to have, especially when using the loader, but not totally necessary. I don"t know if I would buy a tractor without live hydraulics to use, but when I was younger we used a 9N all the time with a loader and sure got by a lot better than with a tractor with no loader. If you plan to run a hay baler with PTO, it might be important to get live or independent PTO, but non-live PTO works OK for running a brush hog with the addition of an overrunning coupler.
I have been impressed with my neighbor"s older Kubota, especially when he brings it over to snowblow when I have run out of room to push snow. It is 4wd and has hydrostatic drive, which allows it to move way slower than my Fords will. He also gets along fine without chains. I don"t know how well that Kubota would work with a moldboard plow, but it sure works great as a small loader tractor. My brother has a New Holland 4wd of about 50 horsepower that he bought new 15 or 20 years ago. It has been a good worker for him and has had very few troubles with it. But the problems he did have were problems that required him to haul it to the dealer"s rather than being able to fix them himself. Even keeping it carefully shedded 95% of the time, the outer "skin" has faded a bit, and he has had some damage to it from objects he ran into in the woods. Is the NH a good tractor? Sure it is, but it cost several times as much as all the tractors I have ever owned combined.
Good luck finding a tractor that will fit your needs, pocketbook and situation. I would look around and see what I could come up with.
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Today's Featured Article - History of the Nuffield Tractor - by Anthony West. The Nuffield tractor story started in early 1945. The British government still reeling from the effects of the war on the economy, approached the Nuffield organization to see if they would design and build an "ALL NEW" British built wheeled tractor, suitable for both British and world farming.
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