I'm not a polaris die-hard, but I have 2 of them, and they represent the budget-window/age that the OP mentioned.
The 97 Polaris Scrambler 500 4x4 I use for plowing also has a trailer hitch ball for the occasional trailer-task. The plow is a very basic skidplate-style mount with a Cycle Country manual-lift lever 48" blade. Even for a vintage machine with original worn 1997 tires, it does a very respectable job plowing on blacktop and grassy areas. This quad has multiple chain-drives; built like a piece of agricultural equipment. Never had a problem with the CVT drive belt or any transmission issues, and it has shifted F-R thousands of times and even flipped into a pond once and sat submerged upside down; started right back up when extracted.
Also should mention, this thing doesn't have a low range; in the snow it will always lose traction before you burn a belt. And for a machine approaching 20 years old, it ALWAYS started every day this winter, even the (many) subzero days that I called it for duty. I must say I am really happy with my Scrambler 500 and haven't experienced any of the 'polaris-lore' mentioned earlier in the thread.
I also have a 2000 Polaris sportsman 400 4x4. As far as used quads are concerned, if you run across a deal on a sportsman of this vintage, they are great machines. The 400 isn't a fast machine; ~55mph tops; but with low range it is a real workhorse and has IRS for a smoother ride. When the battery is dead, the 400cc engine pulls over just as easy as your push-mower. In theory, I should actually have the plow mounted on this machine. Instead, I've used it to play in the deep snow during winter, and it has nice racks on the front and back, and they make an excellent place to set your beer, saws, etc. when the work is done. This machine has given zero issues, and is now 14 years old.
The 3rd quad is a 2wd honda sportquad, and has no provisions to be a helpful wood-processing machine aside from maybe a headlight to help you clean up after dark