One person can do it pretty easily, but its a little unnerving the first few times.
Use the trap line, do not pull on the shroud.
Just grab a trap line, walk away from the boat and pull down. As the boat come over grab onto the shroud, (the side force on the shroud isn't that great at this point as you'll be higher up, and the boat will be somewhat balanced at an angle), then you just grab the mast and walk towards the end until you can set it down.
Obviously check the ground for anything that will damage the hull.