Update on the gelcoat experiment.
I've now done the rear third of the cockpit (between the seats). It had everything from exposed laminate to several layers of failed paint (plus drips from decades ago when the seats were painted). I mixed 10oz of white gelcoat (with wax!) with a few dollops of black tinting agent to get a basic medium gray. After adding 12 drops of catalyst / oz, and mixing well, I dumped all of it into the cockpit and used a spreader to distribute.
As an extra precaution, I sprayed a thin film of mold release using one of those paint sprayers with disposable cartridges.
Result is a bit rough in places but if I want "really nice" I have a set of floorboards to cover it up. As it appears at quick check, no problem with curing and it looks so much better than before. I'd have to work on my technique a bit before trying a deck or surface like that, but because the underlying surface was never totally smooth to begin with, "perfection" wasn't an option but "durability" is a goal. Gelcoat, because it cures by catalyst, can be applied in thicker layers than paint and I'm pretty confident that I'm not going to wear through this new coating.
The question remains what I'm going to do with CB trunk and the less critical areas of the cockpit (such as upper ends of cuddy walls and some of the transom areas). I'll probably extend the gelcoat in all places that can end up with standing water anytime a tarp fails and use paint for the remainder. The CB trunk has failing/flaking paint on it today, in the cuddy, protected from UV, the old paint is in very good shape, except that it's now a slightly different color. My conclusion is that with some practice and good gelcoat (like Evercoat premium one step which I used today) gelcoat can be an alternative to painting the cockpit floor.