Re: stringers
Good question, My feeling is too leave the stringers be and never breach their integrity. I would be afraid that somehow sometime, the drilled holes in the stringer may get water into them and even though they are not cored with wood the water still may wreak havok. I honestly think you will be fine with 4 well sealed screws in each base of the leaning post.
As for the screws holding in fiberglass, It will not hold as well as wood. I do not know the thickness of a 23's stringer but since you would be penetrating the wood deck as well it should hold well.
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