If you are going to be doing alot of illustrator work you might want to get a drawing tablet and just draw directly into the program. Could save a ton of time.
Yeah, but only if I can get my hands on a cheap secondhand.
Don't be afraid to use fonts instead of tracing by hand, especially when your looking for clean pin sharp characters.
The font above must be something freely available.
I haven't thought about that. I have tons of fonts! Searching for one will be the hard part. BTW the 'TM' in my second try is a font, Arial.

This is my second try...

I'm very pleased with it myself, but I like to have some feedback.