I do a lot of illustrations by hand (pen and paper) and I'd like to start using some of this artwork in my web designs.
Should I just draw and scan? Get a tablet? Learn Adobe Illustrator? I find it very hard to draw w/ a mouse.
What's worked best for you?
Don't rely on drawing on paper then scanning it. Invest in a Wacom drawing tablet, you'll wonder how you lived your life so far without one, haha. I use Adobe Photoshop and Illustrator along with it.
I don't have the gift of creativity like yourself, so I have someone do artwork for me and they use a few programs. Namely, Illustrator, InDesign, Photoshop, and Acrobat (yes, Acrobat. I'll ask her why. I think it's for sending drafts to clients for approval).
I think whatever workflow you feel most comfortable with is what you should use.
Scan -> Illustrator -> Photoshop -> ImageReady -> Photoshop -> Save for Web may be a possible one.
My friend, who is a professional comic artist, has tried a couple of tablets, but finds it difficult to adapt to not being able to look at his hand as he draws. It's strange for him to look up at the screen while drawing. So we scan all his work at 300dpi and reduce to 72dpi for his website or send at full resolution for the colourists and inkers to do their magic.
If you have a big bunch of cash, the Wacom Cintiq is without doubt the best solution.
Have a look at one of the digital paint masters, Bert Monroy. His videos show the Cintiq in action.