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I am looking to purchase a late 50s offshore and noticed some caulking along some of the joints on the inside and outside of the transom and keel. Its unusual because it is still tacky to the touch but the owner has indicated that he knows anything about it. My immediate reaction is that this was applied just recently in the hopes of sealing out the hull, but it appears to be in pictures of the boat from 2005. I have attached pictures. Any idea why it is still tacky/wet to the touch?

Some caulking can remain tacky for some time. But not for years. That brownish goo near the transom and the stem is definately not from the factory. They wouldn't be that sloppy.

Sounds like the seller is pulling your leg.

Andreas

I agree with Anreas. Sounds like the owner is trying to sell you a can of worms. Looking at the pictures it looks like there was a white sealer used on the transom before the mahagany stuff was applied over the top of it. I know boat life takes time to become non-sticky to the touch, but even in cool temperatures it is not sticky within a few days.
Very possibly there is a reaction happening between the two types of sealer used.

I any case you are looking at some major work to get the boat restored with leaking around the transom and at the bow stem. Looks like there is seperation on the bow which would most likely be caused by the screws pulling out of the wood (possible rotted wood in stem) or the screws have broken off. Area around transom could indicate that the srews here are also pulling out or broken off and the planking is pulling away from the transom. Again possible cause is rot.

I would take a nice sharp ice pick and start poking around the transom, keil, garboards, stem both inside and out and the rib ends at the kielsons and see how solid the wood is in these area. If it has a floor pull up the floor boards and poke, poke, poke to be sure you have solid wood in these areas. If the ice pick goes in easily then there is rot and wood will need to be replace to have a sound hull.

If you are looking at putting some time in restoring the boat then talk the owner down on price and spend some money fixing it up the right way.

If you are looking for a boat that you can use right now without any work getting it repaired right walk away from it now, better yet run.

Good Luck,

Phill