Had this problem with an O'Day 222
I encountered this problem (thankfully in the summer) a couple of years ago, and it was a result of the outer braid of a double braid pendant rope fraying and then bunching up as it entered the metal tube to the cockpit on the 222. Since the pendant line attaches to the trailing edge of the center board, the board would slide up into the CB trunk without any problem. However, the bunching of the pendant prevented it from being used to pull the CB all of the way into the CB trunk. Once I figured out what was going on, I realized that I could pull the boat onto the trailer and the keel platform on the trailer pushed the CB into the trunk with no problem. I'm not sure what your trailer configuration is, but I assume there is a keel support that should do the same thing, assuming the CB will slide into the trunk without jamming. You might check to see if a line, or better yet a flat nylon strap (I have a 20 ft ratcheted strap that I typically use as a tie down when transporting), passed under the boat will pull the CB into the trunk. You shouldn't need to get in the water to do that. If so, you are in business. You can either secure the CB with the strap and then pull it onto the trailer, or alternatively, let the keel support do the same thing for you. In retrospect, I probably would use the strap approach if I had to do it again just to make sure that nothing got jammed when the boat was loaded on the trailer. You may need to get it on a lift to swap out the pendant, but at the very least, you should be able to get it on the trailer without risking hypothermia. Good luck,Dave s/v Hakuna MatataO'Day 222