Some feedback (I'm going to make some of this general to everyone too because you are bringing up things that need to be considered)...
If the image of a boat is used like #5, it has to be carefully picked. Our user base is split between people with sailboats and people with motorboats. There is no sailor who would want to wear a hat with a motorboat picture on it - they are generally very anti-engine/motorboat. Motorboaters are a little less into that but there is still some amount of "I'm not a sailor". So if boat images are used, it has to be done very carefully so everyone will feel included. For the most part, it's probably better to stay away from them.
#57 is an interesting idea that no one has gone after. The A C flags go well together (I always thought so). The full image there is sort of a sailboat - it's hard to tell. It looks unusual to me like it's a very flat boat with a big mast.
If a boat image is going to be used, it should tend to be an abstract sailboat. See the 3rd general comment about this, boats, and waves.
The rippled flag look would be hard to duplicate on a hat logo. That doesn't mean it can't be used for the web site but it would have to still look OK for the hat if flattened.
We really prefer sanserif fonts. I like how you picked up on the red in the C flag. That's a nice design.
thanks for the feed back, this one was a lot of fun, I did intend for it to look like a boat, not a sail, not a motor, just a boat. I will work with the font suggestion and see if I can give it that "just a boat" feeling. As for the hat concern there are ways to get something like this done and I can present some suggestions after I do the re-work. Thanks again, Bryan [the B]
I like this a lot... I think it represents all sea-farers and lake dwellers alike... makes me want to buy my wife's grandmother's boat ...load up the family, with the lap-top and let ActiveCaptain help navigate me thru the Bermuda triangle... ... hope you like it as much as I do - the B