I'm amazed at how poorly that drain fitting is installed. The way the hose is clamped against the underside forms a trap for debris to collect, and from the looks of the photos, you get a lot of debris. I suspect that if you haven't removed that elbow fitting by now, it is probably clogged with gunk and the flow is restricted by more than half. I'm thinking it looks like the trap on Sue's vanity sink before I clean it out, which has to be done at least once a year (I don't know why she washes her hair in the sink!).
Aside from that, the damage to the fiberglass and gelcoat looks much too significant to have been caused by water freezing on the outside of the drain. It looks more like it is disintegrating from water inside the core that is freezing. Flimsy plastic ice cube trays don't crack like that. When the water is unconfined on the surface, ice won't cause any damage. It is the confined ice inside the core that is popping the gelcoat loose. It sounds like there are some issues with water in the core that should be resolved quickly. I'd look at those drains and want to re-route them immediately. At least the fitting is where you can get to it easily, but I'm also amazed that they put the fitting in an interior finished space.
I would think that for safety reasons, the drain size and the hose could be enlarged and run as vertically as possible to the discharge thru hull, which would also need to be enlarged. Cockpits should drain quickly and there should never be any lingering water. That horizontal run with corrugated pipe is a poor design and installation because it restricts flow and allows debris to accumulate inside the run. It should be modified. I don't know why you would want a grate to trap debris at the drain. I like debris to get flushed through the hose, so I think it is best that they are open. The problem is that you have a trap below the drain. You should eliminate the trap and not worry about the debris. I'd guess one down-side is that something valuable might disappear too quickly to recover. Hopefully, you don't let a ring or other jewelry get detached!