[Capnblu]

Like most things, If you are wondering IF you should, you probably already should have. The failure point will probably the lifting lowering mechanism including linkage points, cable etc. the uncontrolled lowering of the mass of the keel will damage the structure surrounding the pivot point, if the forces are large enough there will be a very big mess to contend with. A loose pivot pin probably is still stronger than the weakest link in your lifting/lowering setup. But never overestimate the skills of the last person who put it back together. The bolts that hold the pin in place can only be assessed by removing them.