I know you mentioned something different than the order of the novels, but I have my own personal twist to the novel approach (to keep things interesting and to include every film). I have not watched them in this order yet, but I hope to when I get around to re-reading the novels again. My logic on some of these might escape some people, so I have added explanations where I feel necessary:
1. Casino Royale
2. Live and Let Die
3. Moonraker
4. GoldenEye (Trevelyan shared similarities to Drax - both felt betrayed by the British although they both originally appear loyal to the crown, both are scarred, both target London, etc.)
5. Die Another Day (Very, and I mean VERY, loose ties to Fleming's Moonraker)
6. Diamonds are Forever
7. From Russia with Love
8. Dr. No
9. Goldfinger
10. A View to a Kill (From a View to a Kill is the first short story in FYEO)
11. Quantum of Solace (Third short story in FYEO)
12. For Your Eyes Only (Takes elements from the second and fourth short stories in FYEO)
13. Licence to Kill (Takes elements from The Hildebrand Rarity - final story in FYEO)
14. Thunderball
15. Never Say Never Again
16. The Spy Who Loved Me
17. Tomorrow Never Dies (I really didn't know where to put this one, so I stuck it after TSWLM, since neither have many Fleming story elements to them - and they both end in giant boat-like bases)
18. On Her Majesty's Secret Service
19. You Only Live Twice
20. Skyfall (Takes the James Bond "dying" scenario/obituary from YOLT the novel)
21. The Man with the Golden Gun
22. The Living Daylights (Second short story in OP&TLD)
23. Octopussy (Loosely takes elements from the first and third stories in OP&TLD)
24. The World is Not Enough (M gets kidnapped, similar plot point to Colonel Sun)