Upgrading Just a Gwai Lo to Drupal 7 from Drupal 6 looks like a lot of work. 10,000+ nodes, combined with lots of functionality (Viewfield) and custom theme work. Lots of dependencies on D6 modules not yet updated to 7.
The current plan is to start all over in Drupal 7.
Tasks for the new site
Move the existing site to a subdomain
edirect everything that starts with the following to the new subdomain:
completely rewrite the about page
"Elsewhere" page, essentially the same as http://justagwailo.com/elsewhere
one page calling each menu
Features of the new Drupal 7 Site
as few contributed modules as possible
Mollom for the contact form
as little custom theming as possible
no more blog
chance to run the Drupal PHP extension
only overrides Drupal 7 with the patch
older versions of Drupal run fine, that is, the functions aren't overridden
no URLs with dates in them
Old Drupal 6 Site
update file system path
update API keys
expire stale content
especially content tagged with 'dead link'
chance to build my Gone module idea
disable UI modules