What makes you think he's confident he can deal with Xykon at his convenience? He has contingency measures in place (like holding the phylactery) just in case he needs them, but he seems to be more confident that he won't need them (because he imagines himself to be a master manipulator), than confident that they will work.
All of those opportunities happened before Gobbotopia was established.
With the exception of the first one, they happened during times when no viable alternative to The Plan - or even a meager substitute for The Plan - was available to Redcloak.