WorldFallz - November 29, 2009 - 07:19 Upgrading is definitely more complicated than it should be, but I wouldn't say 'extremely'. And the downside to staying with d5 is that it will be end of life as of the release of d7.
1. Update all modules to latest version. 2. Backup database. 3. Download all site files. 4. Disable/Uninstall Update Status Module. 5. Disable all contributed modules. 6. Switch to Garland theme. 7. Delete D5 files, saving sites, files and any extra folders or files I added. 8. Delete D5 contributed modules 9. Upload latest Drupal release files. 10. Upload D6 versions of contrib modules. 11. Go to /update.php and select continue then update. 12. Review update messages for significant errors. 13. Review modules and enable those compatible with D6. 14. Enable new (but optional) core update status module. 15. Check contributed theme status and update if necessary. 16. Re-save blocks and position. 17. Rebuild any previously built views. 18. Bring the site back online.