Ok, I get the proposal now. But, it's hard to get behind any idea that intentionally brings more water INTO the boat. On land or sea.Ken has a good point, though as I understand it, your winter storage is on land.
Like Jeff said, all that PVC is ripe for replacing, but the first thing I'd get rid of is that U-loop in the drain. Can't imagine what purpose that serves, unless the PO who installed it couldn't achieve tight-enough hose bends to make a more direct connection. I'd try something more like this:

My port outboard scupper had an extremely tight S-curve in the hose. I couldn't find a high-quality 1.5" hose that would bend that much, so I cobbled together some pre-formed silicone hoses (45 degree and 90 degree silicone hoses from Amazon). And I got rid of the PVC elbow in the process.

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