It's the Cold War in the Alpha Quadrant, and our heroes attempt to gain strategic advantage without triggering a quadrant-wide conflict!
The Winning Entry:
Salus Populi Suprema Est Lex
From my perspective, you absolutely NAILED Garak.
The Dominion war was the only time he ever, truly allied himself with his 'friends' on Deep Space Nine, and even then he was still fully capable of betraying them at any time. I think the fact that he didn't had a lot to do with the fact that his primary opponent was Dukat.
Your not-so-chance meeting between Garak and Bashir is exactly how I would expect Garak to behave... the war is over and Cardassia needs what it needs. So he's essentially working to look out for its best interests. And he's Obsidian Order to the bitter end... never mention anything you don't absolutely have to, and manipulate people whenever possible.
Recently I rewatched the entire series and was surprised, even in early episodes from season one, seeing how hard Garak worked aboard DS9 to protect Cardassia's best interests... even after they had exiled him.