I look at used tractors online, a lot, and still, I have to say they scare me off. Tractors hold a good deal of their value. A LOT of people buy tractors that are too small and then beat on 'em. A lot of loader buckets look like they have been through a war. Part of buying a new tractor is the warranty. It adds a level of comfort that a used machine would not. I'm not particularly skilled or patient with mechanical stuff, beyond normal maintenance items. I would never consider splitting a tractor, for example, even a small one. At my age I would expect any new tractor purchase to outlast me by a lot, and I would expect that my current tractor should last at least another 15 years. When I bought it, I christened it "the last big toy before the dirt nap," but now it appears there will be one more if I don't keel over in a matter of days..
My tractor has made one trip to a dealer in 15 years, but it wasn't the one where I bought it. They went out soon after I bought it. Ease of getting to a dealer is a matter of concern for me, even if I'm lucky enough to not have to get there. If I didn't see local dealers here for decades for about every tractor or implement you would ever need, I probably would be much less concerned about distance. Local dealers used to come right out and fix tractors right in the field. You don't see much of that going on anymore. Used to be itinerant tractor mechanics in the yellow pages not long ago. They seem to have gone the way of doctors' house calls..