I will be discussing problems and possible solutions in my effort to save a 1978 Chrysler C26 swing keel sailboat. Please bare with me, this will take some time.
Legal stuff.
I offer my fixes to the problems found on my boat. Do not attempt these fixes unless you are familiar with using epoxy and polyester resins, fiberglass cloth and mat. Read all safety warnings regarding these materials and their use, the same goes for using power tools. Proceed at your own risk!
Probably the single most important thing to know about a fiberglass boat is, that it is not all fiberglass! Wood of various types are used extensively in the manufacture of production run boats, whether power or sail. If you drill through the deck to mount hardware, you will likely also be drilling through plywood, end grain balsa or in the case of the Chrysler C26 a phenolic honeycomb core. If the hole is not sealed with a epoxy or polyester filler, you are very likely to have water migrate into the core material. Silicone and other sealers can not stop this in most cases. Checking the inside of your boat for leaks around hardware does not mean that water is not leaking into the core and damaging the structure of the boat.
The rudder needs extensive work. The pivot hole was badly worn and it had fought with the outboard and lost a few times.
Epoxy-glass bushing