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· Asleep at the wheel
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When I did the original logo for Dragon Wing, which we used on our Catalina, I found a picture of a C25 from the side. I then used the height of the winch, which I knew, as a reference for approximately how high my different lettering was. So, for example, if I wanted to see how 4" lettering looked, it was about the height of the winch (if I recall correctly). If I wanted 5" lettering, it was one and a quarter times the height of the winch, etc. I then drew lines on the picture (in Microsoft Word, but you could use Paint, or do it by hand) that were that distance apart, then fit the font size to match the distance between the lines. That gave me a good sense for how big the letters would be.

As the others have suggested, I used Boat U.S. twice now, and have found them to be excellent. They have almost every font, including some really obscure ones (like the one we used on Dragon Wing). They can also take third-party artwork, assuming you have the copyright rights to the artwork.
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