Greenlake - yes you are right, it is a game of inches. Anyplace you can save some drag is important. The aluminum cheeks are rounded and thin to slice the water if they stick down below the surface of the water minimizing drag. The newer aluminum cheeks on the latest boats are squared off at the bottom like what you said. Woodie is a "gentleman's" racer, I'm looking for style points. Which brings me to our next subject - Coamings
Woodie had these goofy wood coamings screwed to the side of the cockpit for looks. They probably looked good sixty years ago but looked pretty sad. They actually have a purpose on these old DaySailers as these boats have just enough buoyancy when swamped to float, barely. The old coaming was really tall, like six inches tall so they would stick high enough out of the water allowing you could to bail the boat out. If you cut down the coamings, you lose this function and need more buoyancy to self rescue.
I looked at the coamings on Woodie and they would be expensive to replace and the wood in the inside didn't look quite so bad and could beach out, so I reversed them. The port one is now on starboard and vice versa. I cut down the centers for hiking out and left a little height in the back. I found if you turn sharply and take a deep cut at the leeward mark, the stern swamps with a lot of water, very quickly. This riser should deflect some of that water.
You probably noticed a little addition besides the riser, I added a wood skirt. The wood coaming is really flimsy so the skirt adds a lot of strength and not a lot of weight.
The skirt adds a little height and I couldn't get the edge of the coaming to look right by itself. It just looked like it was cut down. I guess I should have left the edge proud about a quarter inch but it was already cut down when I got the boat and wasn't pretty. This modification isn't difficult, I took a 3/8 inch board and scribed the inside edge and made another cut about 1 1/2 inches parallel to it. Then glue and clamp in place with some parchment paper to protect the fiberglass. Sort of used the deck as a mould.
You need a lot of clamps. I used West G-Flex Epoxy mixed with some sawdust to thicken as there were a few gaps. I then used some fiberglass tape to reinforce the joint on the inside and it is quite stiff because it is joined from two compound curves. This would be a great way to strengthen this edge on the later O'Day DaySailers - the ones without all the wood.
Starboard side, roughed out and reinforced with fiberglass tape. You can see some of the tape on the bottom edge. I think it will soften the edge when finished and help fool the eye into thinking it is seeing a wooden boat. Now if it would only stop raining ......