I lived aboard a classic 1956 Chris Craft Connie for 5 years and am very familiar with wooden boats. When a wooden boat is taken out of the water and “put on the hard” for painting or bottom work the wood shrinks as it dries. When we put them back into the water they are left in slings for sometimes up to a week with pumps in the bilge to give time for the wood to re-swell which tightens the seems back up. The packing we put between the boards cannot be too tight or as the wood swells it will buckle.
Wow! It's a dream of mine to have a wooden boat such as the one you lived on. People always tell me how impractical and hard to keep up a wooden boat is and try to pop my balloon. I think the romance of one might just be worth the trouble.