Mast step area
Is the boat in or out of the water? The mast step looks pretty good to me. Take a bottle of water up there and pour it around the mast step. It should not pool. Pooling might indicate depression of the mast step relative to the deck. That would warrant a look under the compression post. Also look at the turn buckles. If they are adjusted tight the boat could be deformed temporally. Also if the turn buckles are near the max of their range, it could indicate continual tightening as the deck deforms under the compressive load.
There is no wood core under the mast step. Just a steel plate embedded in the glass with threaded holes for the bolt. I went through ALL of this over the past few years. Check my posts. My conclusions after cutting my floor open and finding that the blocks under the post were fine, and cutting my deck open and finding it was fine were (a) Geometrically the mast is in FRONT of the compression post (lousy design) resulting in less than ideal support (b) Water which leaked in through where some past owner drilled a hole for the VHF wire next to the mast had wet the core. I had sealed it and it was dry, but the balsa had dried and baked to dust resulting in the depression I was seeing in the deck which was due to (a) as well. (c) My rigging was probably too tight adding downward pressure and (d) my concern that my head door wasn't hitting the stop on the cabinet opposite was more likely lousy carpentry in the 80's than anything else!
Get a cheap boroscope on Amazon for $30 and run it over to the post from the head drain to look at the block under the mast. I think it is possible.
@BobM thanks for feedback - I went back and looked at your photos. The mast is coming down next week to move the boat to Erie. I was able to see the area through the transducer hatch and from the storage area under the seat. It looks like the plywood layer and sole was damp and crushed down slightly. It had been raining two days prior to me looking and there is some staining of the sole. The area underneath the post is a large support wrapped in glass. I didn’t see any depressions in the deck. I added some photos showing the area around the column. I didn’t take any pictures of the sole and plywood but I think all this local depression is simply from the wet layer of plywood and sole.

I will check the area where the cable passes through hole and seal that off and check for any water damage there. Since the mast is going to be off I can remove the mast step plate and inspect wiring and seal that as well when I reinstall. When you reinstalled Mast step plate on the deck did you seal it in any way? It looks from photos there was no sealing or bedding used when installed originally - I assume this was intentional due to the mast loading.

I followed the advice on inspecting the bulkheads where the chain plates are and they all seemed solid except the forward one on the port side in a cabinet in the head. That one will need some attention. I plan on removing the chain plates and performing an even more thorough inspection and then reinstalling and rebedding - assuming nothing is found.


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