You guys do such an awesome job of "breaking it down". I know you are both interested in a G&G Re-Design. What about a podcast series, with screen cast sister podcasts, and forum posts (innovating tomorrow) code and programming related...
Like a TV series that crosses over episodes :)

ready for this....

Redesign in Drupal 6

G&G Podcast 1: evaluating your current set-up, planning, development
ScreenCast: A backstage view of G&G, modules, config, tweaks, theming functions, custom code.
IT Blog: some code used to keep G&G going... until the upgrade was possible.

etc.....

You would have time to do the redesign, and we would all get to benefit from your experience. It's a reality show meets podcast...