Other than blown rotted Valleys, my leaks have been rim to kayak leaks. Like Andy, I have a Kajaksport kayak (mine's a Viviane), and it's got a large oval on the front, and an extra large oval on the back, and they don't leak. P&H seems to have had issues sealing the rims to their kayaks, at least for a time a number of years ago anyway. I resealed a couple of mine and one of my friends, I believe all of the '03 to '06 years. I think the round ones are a little less ugly on the deck, but I think function outweighs my personal opinion about looks.
If I were building one, I would certainly note a couple things. Leaks between the rim and kayak have shown themself to be common in my experience. All these tupperwear lid covers can be a bear to put on and take off in some situations, so you commonly see a lot of pressure put on them, including things like smacking them with the paddle as noted above. So the intallation of the rim has to be very, very solid.
URCHIN Portable Anchor
Kayak & Canoe Outriggers
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