Re: new to me 1969 Cheoy Lee Offshore 27
Some pictures of the concerning areas of the bow and stern pulpits would help. I know some people re-pack their stuffing boxes in the water. But, water will come in while you do the job. I would be worried about getting in done right the first time in the water. At some point you will want to take a look at the bottom yourself. Just combine all the projects that are better done out of the water, and have it lifted. If it is OK to sail now, then put off the projects until you have had some fun with the boat.