I careened my boat all alone last week. I left the mast up, tied the transom cleats to an anchor about 30 beet back, loosened the winch a few feet, then pushed the boat back on the trailer a few feet until the slack was out of the winch strap. I then pulled the trailer forward by hand. The boat slid back further along the trailer, with the winch unwinding as it went. When it was near the balance point, I locked the winch, then by hand tilted the trailer and boat until the transom was on the ground. I then unlocked the winch again, and again by hand continued to pull the trailer out from underneath the boat. The last few feet are the most precarious, but managing the height of the tongue by hand, you can settle the boat down onto a couple of fenders along the keel line. I also placed an old tarp under one side, a camp mattress, and a couple of life jackets where I thought the boat would eventually roll onto its gunwales. I pulled the trailer away from the boat. With the mast up, and using the sail end of the main halyard, (the inboard end secured to a cleat), I started walking backwards to the side of the boat, even with the mast. Eventually you run out of rope, (halyard) so continuing to walk backward, you also have to pull down on the halyard to start the boat rolling. It is relatively heavy at first, probably about 50 pounds of pull, but as it starts to come over, and rest its gunwales on the life jackets, you could likely use a construction block to tie the halyard at the top of the mast down. I just tied it to my neighbours trailer.
Getting it back on the boat is just the reverse. Carefully let the boat back down, then position the trailer so that it lines up with bow, attach the winch/tow hook, lift the tongue of the trailer and snug up the winch. Then crank the boat back on, making sure to keep it centered.
Here is a picture of the boat careened.
http://groups.msn.com/RogerConrad/shoeb ... PhotoID=96