Hey @Steggs101, just got done watching your video. Your ship is shaping up nicely. I wanted to chime in with some tips for your sails;
This is how you have yours;
And this is how I'd do them;
If you prefer that method, you can achieve the angled slant with these chisels;
As for the 'S', I'd go with simple digital font. It's much cleaner and easier to read. You also wouldn't have to emboss it;
Trust you to make things far more complicated than they have to be! Hope that helped, bud.
Edit; Erm.. @Scratchnwiff... I made a mess on your island...