I really like your project, I think a scepter might be my next boat.
If I do one, I will paint the window frames as you did and source some new glass.
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I don't see too many on here painting bilges or if they are, they are painting them the same color as the fiberglass. Is there any downside to painting it? I am doing so because I want a clean look and I want any debris to be easily visible.
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lots of nasty things end up in the bilge, things that are mean to most paints

most topside paints will not hold up in there. I prefer to use pigmented epoxy, its fuel resistant (you can make gas tanks with it) and it cleans up very easy. It also bonds VERY well.