No need to apologize for liking stinkpots. They have their place -- especially the fishing variety.
Sorry, but I don't like the idea of re-attaching that cleat with screws into the fiberglass. Despite how you expect to use it, it will only be a matter of time before it gets a good yank and tears out again -- maybe making things worse than they are now.
Some builders do use screws for attaching deck hardware, but they normally will have a backing plate with tapped threads that the screws set into, rather than relying on grabbing into the fiberglass (which doesn't really work well).
There has got to be some way to minimize the invasive procedure of getting access to the back side of that cleat. Or, could the cleat be re-mounted in a somewhat different location, where access is better? Whatever you end up doing, be sure to add a backing plate.
Hopefully MaineSail or another savvy maintenance guru will come along and offer some better suggestions. Good luck!
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Pacific Seacraft Crealock 31 #62
NEVER CALLS CRUISINGDAD BACK....CAN"T TAKE THE ACCENT