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5500 Canadian is about = to 5500 US. Seems kinda high if it is bare bones but not completely outrageous....Last time I looked a '07 500 was about 8500 Canadian. a good winch is about 150 - 300 and a plow 700+ throw a back seat on for another 300+, and what about tires, I am guessing stock, so there is a bit more.(these are new prices, so you may get used cheaper). And yes a brain protector is a good idea....price varies to your preferences. If you look around you could prob get a different bike with the majority of the add-ons you want for less money than you would be spending for this one.
Hope that helps a bit.
Hope that helps a bit.