Hi, Zack,
If the plywood is wet, it will
rot and the
rot spreads pretty fast. So, rightfully scared, imo, you need to get a look at it soon, don't put it off. Then let us know what you find. If it is damp, you have to dig out the wet plywood as far as it has gone. Back to where you can chisel out dry
wood. Leave as much as possible of the
fiberglass in position, because you're going to re-core it. (The more you take out, the harder the job will get.) You want somewhere, preferably, where you can get the boat under shelter, or you're going to have to figure out a way to keep it dry should it rain. You're in luck, rains don't usually start till this month in So
Cal, and often not till Dec.
So, next time you go to the boat you'll see what happened, and remove the roller. You'll need something to sound the
core with, like a tack hammer, even a 1/4" drive rachet handle will do, or a pocket knife handle. You go tapping from the damaged area towards the stern with your tapping. When it goes from a dull sound to a hard, sharper, sound, you've found the edge, where there is solid plywood. You will need a big piece of cardboard to make a template, for your new
core, and you'll need to know what thickness of
marine ply to buy. [If you're lucky, someone may have an offcut that is big enough. It's worth visiting around and seeking out.] Be prepared to tarp the boat very well, because the things you have to do at home after
work, will take some time.
If there is no rot, then your job will be a lot easier. And, yes, both windlass and roller should have backing plates, and so should the stem-head fitting. When you get them off, you can find out what you need for backing plate material (what will fit in the spaces you have), and how to mark it for the bolt holes. You are likely to need a size or two longer, depending on the thickness of the flat stock you buy. When you're done, it will all be stronger than ever.
Good luck with it, but the longer you let it go, the worse it will get. I hope you don't fall in that trap.
Ann