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The Old Man and the Sea...and Me

First off, let me share something that is probably readily apparent...I have zero art/design background.  I enjoy typography, design, etc and when I saw Ms. Hische was teaching the class, I was in.  Plus I always want to learn Photoshop & Illustrator better.

Anyways, I love The Old Man and the Sea by Ernest Hemingway and wanted to do that book.  I chose to use "H" for my drop cap letter without really giving it much thought.  As I started my sketching, I came to view it as a very square, symmetrical, rigid letter.  Could be my lack of artistic inspiration but that's how I felt. 

I did come up with a sketch that I liked.  I had an idea to do something that would involve the negative space of the 'H'.  I thought that if the H was curvy enough, the inner white space could be the boat.  So this is my sketch from that. 

I would LOVE any feedback, the more basic the better.  :)  Don't worry, you won't hurt my feelings! 
I am curious as to your thoughts about the fish.  Should it be similar to as shown (a top view off to the side of the H), or should the fishing line just run to the cover edge, or shoud it run to a spot and then stop like it is going down into the water?

Anything else you can offer I'd benefit from would be appreciated.

Here's my first rough draft of a digital version.  Colors are not actual (I am trying out the 'global swatches' that Jessica shared about.)

I know it is super basic but any helpful advice or critique would be great!  Thx in advance.

Iteration #2:

New colors, better boat negative shape, straightened outer edge of letters, larger Old Man, new hat.  attempt at ripples.

Iteration #3  Improved the ripples (a little), worked on the boat shape, seperated the crossbar to help stress the negative space outline.

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Iteration #4 - tried some blur on the ripples and spaced them out more, added some wavey texture to the letterform, worked on the fishing pole & line and made some adjustments to the Old Man (gave him arms and shorts!).

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