Greg, there's no question of outstaying your welcome at all. There are many people in the US who have no personal access to other people with DaySailers either. Not everyone is in a fleet here, or even a region where a significant number of DS are being sailed. Now to your question.
I'm afraid your idea isn't as sound as you might imagine, because when sailing there's a kind of backwash going on that pressurizes the forward top of the CB trunk. Nothing a check valve couldn't take care of, but then you might as well have routed the discharge directly through the hull.
DS2's have a very narrow opening for a CB uphaul at that location and DS2 owners are perpetually unhappy about it leaking - sometimes so substantially as to be "squirting".
Are you planning this installation for automatic operation when the boat is moored or docked, or do you imagine using it while underway? In my experience a DS1 unless sailed in the rain or in very choppy conditions doesn't tend to take on significant water. Exceptions are when you start burying more than the rail (or do a full capsize) or, when trailering, if you lower it in the water w/o fitting the plug first

In case of a full capsize, an electric bilge pump may not be the answer -- I imagine the batteries might not like being immersed.
Just thinking out loud here. More useful input if you can clarify your scenario.