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Dont go out on 1 sled ever, unless you like hiking a long way home, and esspecially if you are spending 2 g's. your sled will be a piece of shit for 2 g's. I recomend a 2005 or better ski-doo summit 800 with a minimum of a 144 track, id go with a 151, for sled skiing especially, sometimes you goda get up some gnarly shit so that you can go down some gnarly shit.
As for a trailer, they work but they are a huge bitch, its way easier and less hassel to get a pick up.