The “semi-official” WordPress major upgrade path:
1. Backup the files and the database.
2. Download WordPress 1.7.
3. Do a manual upgrade to WordPress 1.7.
4. Repeat step 1, but don’t replace the previous backup (keep both on hand).
5. Download WordPress 1.9.
6. Do a manual upgrade to WordPress 1.9.
7. Repeat step 1, but don’t replace the previous backup (keep both on hand).
8. Download WordPress 2.1.
9. Do a manual upgrade to WordPress 2.1.
10. Repeat step 1, but don’t replace the previous backup (keep both on hand).
11. Download WordPress 2.3.
12. Do a manual upgrade to WordPress 2.3.
13. Repeat step 1, but don’t replace the previous backup (keep both on hand).
14. Download WordPress 2.5.
15. Do a manual upgrade to WordPress 2.5.
16. Repeat step 1, but don’t replace the previous backup (keep both on hand).
17. Download WordPress 2.7.
18. Do a manual upgrade to WordPress 2.7.
19. Repeat step 1, but don’t replace the previous backup (keep both on hand).
20. Use WP’s automated upgrade to system to upgrade to 3.0.