With Drupal 7 around the corner, a lot of Drupal developers and users are surely looking at their lingering still-on-Drupal-5 sites and thinking, "surely I might be able to skip Drupal 6 and upgrade directly to Drupal 7?"
Most all experienced Drupal developers would say (to end-users), "not possible". This is because modules only provide upgrade paths from one major version to the next, and just about all Drupal modules received large rewrites between Drupal 5 and Drupal 6. Without help from module developers, it's not extraordinarily difficult to do a direct Drupal 5 to Drupal 7 migration, but you are going to be building out a lot more things manually.
Of all the projects I'm working on, only my personal blog was still on Drupal 5. As this is rather embarrassing, I figured at least it would be a good experience with direct migration from D5 to D7. Here are my experiences and the approach I used in this upgrade.