I agree with the busy part. How would those pictures show up on a shirt?
I would like to see something that shows the basic lines of the seacraft, hull only maybe. Also I vote for a 20' hull because the last two shirts were 23's. Granted the 23 hull is famous but I am partial to the 20's.
Maybe a side profile with the lettering like you are showing. Or the original script like the original emblem that 65 Bowrider has. I am sure collectively we can come up with something.