Can't see the tire on the trailer but the lack of suspension on the axle indicates that is not designed to be towed on the road. I doubt if your Sportsman would fit in that trailer very well. Just my opinion from what I see in the picture and I could be way off base.
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Plumb stock Prairie 360 cept for the winch, snowplow headlights, hard boxes, alarm system, snowplow and bucket mounts, trailer hitch, sprayer wiring, cow prod bumper, horn and extra tail/brake lights. Survival gear, fence fixing equipment, spare fuel and water racks, GPS, CB, fender bags, rifle boot, chain saw rack, rope rack and tire chains.
I support the Bill of Rights in it's entirety. Loose one, loose them all.