Dealing with an unaggressive editor

I wouldn't go behind an editor's back. That is not the way to do things, but when rejected I would tell him that I intended to pitch the story idea to the next guy up the ladder. The "may work" is just too passive-aggressive.

Either one of two things will happen. You'll write those stories despite your editor, who will likely be pissed, or you won't write those stories because of your editor, who will likely be pissed, and you'll just quit for another job within six months anyway.