Before you get started I recommend that you take a look at Greg's upgrade video at http://www.masteringdrupal.com/screencast/upgrading-to-drupal-6. I watched it and it definitely helped with the process.
The upgrade process took me two hours. If you are using Drupal for a single user blog site, and are making minimum use of CCK and Views then I think that you should be able to execute the upgrade in the same amount of time it took me. If you're running a community site with a lot of content, a few custom content types with associated views then you're probably looking at three to four hours.
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