This is so way the last theme I do by hand.
After putting it off for, well, nigh years, we've finally decided to do our corporate website. We so way needed to do this like 18 months ago. Silly us.
I have a design that I'm partial to, which is just the plain HTML. My thought on doing a Drupal theme is to start with the HTML and replace the static text with the dynamic text. Doyle takes an existing theme and modifies it to do what he wants.
I'm not sure which approach is better. If I had to guess, I'd say Doyle's is, because I nearly hate doing themes, though I'm not 100% confident of my HTML/CSS either.
Just 95% confident.
Time for that theme generator.