ATV: Where my cabin is; roads are snowed in during the winter and it's snowmobile or ATV. ATV's get around just fine if AWD. They are not legal on groomed trails in our state, consider that.
If the trails get high usage, they get bumpy and the newer sled has much better suspension.........For your useage and price range, you can't go wrong with any Artic Cat, Polaris or Yamaha in the years of about 1999-2003. A 700 would be a good size if hauling 2up.
Snowmobiles pic's from 3 days last winter near my house:
Picasa Web Albums - robert.seelye - Galagher-Blew...