I suppose there's a chance of rotten core beneath the pedestal guard as a result of that fitting leaking over the years, but it wasn't detected during the survey. I'm hoping it's just a matter of rebedding the hardware.
These links will take you to Maine Sail's website. From what I've seen, he's done the best job in documenting the process. He shows using a dremel tool to displace the core material in order to seal the deck, but a bent nail is often used as well (putting the nail into the chuck of your drill).
Sealing Deck Penetrations to Prevent Core Rot Photo Gallery by Compass Marine at pbase.com
Re-Bedding Hardware Photo Gallery by Compass Marine at pbase.com