I don't really need the chocks on the sterns at that point - only when I move the hulls to where I need them do I need the chocks (when I slide the hulls back off the dolly to the ground for stability). The hulls go straight from the trailer cradle to the dolly cradles.

The absolute beauty of this system is that you back the boat to the water, with the cradles right at the edge of the water, lift the bows, push back, and launch. You leave the wheels right there pegged in the sand. When you return, you don't have to beach the boat. Jump off in the shallows, lift the bows onto the cradles, slide the boat forward, pin the dolphin striker, and wheel away.

However, I mostly sail on lakes so I don't have to deal with a tide.