Despite worrying, planning, and putting-off upgrading this site from Drupal 5 to 6, the actual upgrade took less than an hour, including the backup and migrate. There was only one puzzling hangup. After 15 minutes of searching, I realized that I needed to turn on the taxonomy mod and everything finished upgrading without errors!
I'm still upgrading modules and turning them on, so some site functionality will be missing for a while. I will also take some time to re-architect some of the site and maybe finish some ideas that weren't easy in D5.
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