You'll feel better
Jerry: You will feel better if you check or have the pin checked in your keel. Especially if you read this fourm often. I checked mine about 2 weeks ago, and it looked about perfect, with barely a scratch on it. The hole in the keel was only slightly oversize too, so I was happy. This is after 20 years most of which were in slightly salty water on Middle River on the Chesapeake. It's my opinion that many of the pins and cast iron keels that people say "wear" through, actually are "eaten" up by Galvanic corrosion, the corrosion that occurs whenever dissimilar metals are in contact with each other, in a corrosive environment. The installation of zincs near (and aft) of the pin is really important, in my opinion. I have 2 sets of the domed, ~2 3/4 inch diameter, zincs on my keel, and replace one set every year. After 2 summers, a set is really eaten up. The 4 stainless steel screws came right out of the bronze pin holders on my boat. Catalina Direct sells the screws, and the pins. They recommend 30 foot-lbs max. torque on the bolts. I would check that if I did it again. I did use a torque wrench, and at 30 ft-lbs.,it seemed like the bolts were stretching more than I would have liked. We lift our boat with 4 big winches using chains that are lined with carpet and then thin plywood, so I can't help much with advising you on how to do it with the boat on the trailer. We used the keel winch on the boat to keep the keel vertical, and had a floor jack under the front (top) of the keel when we lowered it about 4 inches, keeping it just under the boat. This went well for my wife and me, actually a lot better than I thought it would. I think you should buy the pin and screws and have a yard help you, if doing it on the trailer scares you. Aldo