Leaky clinker planking

When I bought her she had been stored for 7 years and leaked a bit. I scrapped it all off and painted it, of course the leaks were worse. She had been a hire boat, so tar was fine. However, I saw privately owned boats that were beautifully varnished and wanted mine the same. Vanity has been my downfall.
 
I'm always puzzled by the concept of refastening hard to stop leaks. If the nails are tight when the wood is dry, won't swelling cause exactly the same strains as just filling the gaps with something solid?
Or if the nails are tightened when the wood is wet, they will loosen when the wood dries so there will still be a leak.

Obviously nails that are loose even when the wood is swollen need replacing, but otherwise the choice seems to be between something flexible, or just living with the leaks until the wood has swollen again?
 
When Constance (larch clinker planking) was being built I asked Fabian Bush to liberally apply boiled linseed oil to her, as I had heard that 100-year old boats so treated are found to be good as new when stripped of paint, and that it might also effect some permanent take-up. So far she has come ashore for two spells of 7-8 months, and both times remained virtually bone-dry on return to the water. You might consider taking your planking back to bare wood and doing the same before repainting or varnishing. But if varnishing don't go mad or, as we found in a few interior spots, the varnish may adhere poorly and form bubbles. Paint seems OK though.
 
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