Mark, the main thing I notice in the photo of your boat docked next to Charlie's is the angle at which each is sitting in the water. Yours is sitting fairly level, while Charlie's bow is sitting fairly high. (At least, when Charlie's not in the boat.
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The reason this is interesting to me is because my DR recently starting taking on much more water when it sits overnight at the dock. Used to be I would come out in the morning and find maybe 2" of water in the transom - which I pump out with an electric bilge pump. Now I'm finding 5-6" of water in the transom - enough to reach up past the rear seat. It's enough that I worry if I forgot to check the boat every 8-12 hours, it could sink!
I've been asking myself why this has changed, and the main thing that comes to mind is that a couple months ago I built a new front floor for my DR using old wooden water skis, which are probably about 1/2" thick. My prior floor was made from 5/16 oak flooring, and the new one is noticeably heavier than the old one. I've always suspected that most of the water that leaks into my boat overnight is coming in where the wet keel & the dry keel meet under the front deck (which unfortunately is forward of the bulkhead). And I'm thinking the extra weight of my new floor may be making the difference between that part of the hull being up out of the water vs in the water when the boat is tied up at the dock.
I've lived with the "minor" leak for years since getting my DR. But I'm not comfortable living with the new mo major leak. I think my first solution is simply going to be installing an automatic bilge pump. But at some point I fear I may actually need to bite the bullet and fix the leak!