Well, in regards to 'Obsecurity' not trying hard, let's consider your points, the card, and conditions of the war.
1 - Recovery Card Boss Monster:
The understanding of a recovery card is that you have failed to beat the level/opponent/etc prior to your win condition. Being in Obscurity (the center of alpha males), we don't need to recover. To recover is against alpha male policy. This is man territory.
2 - Dropping Gems early on a card:
You mention Killin' may not have dropped as many gems if they knew. Shame really. GI Joe: "Knowledge is half the battle"
3 - Obsecurity:
Pls -_-;