In Photo 3 (#246) the track is out of the hole and the front of the sled is actually starting to swing downhill, which is what you want . a change in direction from pointing uphill to downhill.
By Photo 4 (#249) the sled is starting to roll and is totally out of the hole. In deep snow, the windshield and hood just push gently into the powder. However, if the snow is a little more set up, some prefer to remove the windshield rather than risk breaking it.