I agree that the cracks are due to the underlying fiberglass flexing, but disagree that it represents failure of the laminate, or even failing of the laminate. Gelcoat is so ridiculously easy to crack, that there probably isn't a boat here that doesn't have a gelcoat crack here and there. So the laminate is flexing, but not beyond, or close, to the margins it is capable of repeatedly cycling. There is no indication from below that the glass itself has any issues.
But we agree that this flexing should be addressed because, well, just because. It's the right thing to do. There is only 2-3" between that winch pad and the locker edge, so 4-5 layers of additional glass under the pad isn't going to do anything, or spread much load in that direction. It would take 8 layers or so of 1708 to make 1/4", and more if using cloth.
What is required here is a thicker, stiffer laminate extending to the edge, and this is easily accomplished by by cutting a piece of 1/4" fiberglass, let's use G10, so that it fits the circular winch pad area and extends to the locker edge and fore and aft a decent distance. Now let's use thickened epoxy, say a tube of Six-10, and stick that piece to the underside. No need for sewing needles, etc - just use the existing bolts to hold up until cured. Of course, prep the surface for adhesion, but even adhesion isn't completely necessary here. There really won't be enough shear forces between the layers to matter, but adhesion is good regardless.
For this method, the only real skills and supplies needed are a small piece of 1/4" glass sheet (Mcmaster-Carr), a jigsaw with a few blades (the fiberglass sheet is going to dull them every foot of cut or so), and a tube of Six-10 in a caulk gun. Everyone can run a jigsaw and a caulk gun. No learning for the first time to use and mix epoxy, properly wet out stitched biax, and undergoing the frustrating learning process of glassing curved areas upside down (with epoxy - this is much easier with polyester). Also, the health issues with epoxy, particularly for a new user who hasn't experienced all the ways it gets on skin and through protective gear working upside down, goes almost completely away.
I do a lot of work in both polyester and epoxy, and carry both on board. Several versions of each, actually. They all have their places and uses. I'm not for or against either, and learned to glass with epoxy. I've probably done more epoxy work than polyester. People who have primarily used epoxy and are experienced with it often forget just how demanding it can be. There is no ability to control wetout or cure time, it wets out much slower than poly, and no ability to control gel time to better work overhead. When epoxy wetouts begin sagging and falling, there is little to be done other than start over again with fewer layers, or perhaps hang around for hours and hope to catch the very short gel time where they might be restuck and hold, but probably not. If needing multiple laminates, and not using peel ply, then unlike polyester the laminates need to be prepped between each layer. Get that wrong, and you have problems.
Mark