I'm thinking that the previous owner bought a tiller for this rudder that was wider than the original tiller, and in order to get the desired fit in the rudder head, he may have raised the rudder head by lowering the pintles. I did the same thing to my rudder years ago. This would give the desired clearance between the top of the transom and the underside of the tiller, but it would raise the rudder blade to a point where you can't take it off. The only cure for this problem is to buy a tip up rudder. You should be able to un-ship that rudder without having to remove screws. As for the centerboard pendant line, you need to get part of the boat off the trailer to get at it. This task is easier with a roller trailer and two, or even four sailboat stands, some rope tied to the stern of the boat and a tree or something solid. You would need to use the towing vehicle to pull the trailer out from under the boat. The rope tied to a tree keeps the boat in one place. The boat stands placed two on each side of the stern will keep the boat from tipping. I would place blocks under the stern to carry the weight of the boat. It's quite possible to get enough of the boat off the trailer to let the centerboard down and replace the pendant line, but it can be dangerous. The easiest and safest way to do this is to bring it to a boat yard and have them lift it for you or have them do the job. Of course, you'd need the new pendant line with the shackle before hand. Unless you have the equipment at hand and the means to do it at home, it's not an easy task. If your trailer is a bunk trailer, You would have to jack up the boat from the ground and move the trailer ahead little by little until the centerboard can be dropped. If you decide to do this yourself, have someone help you and do it as safely as you can.