Rather this is deciding *how much* drama there is in the decision point. The fact that you are having a contest at all is what makes it a decision point. But possibly I was misunderstanding your original statement "I don't think my ability to become an initiate ought to depend on when in the story I decide to do so." I took this to mean "Becoming an inititate should be a fixed resistance, because it is not easier to initiate if you have been having a really bad day", whereas I think you actually meant "I don't think becomign an initiate should ever require a contest, because if the player wants it to happen then the 'no self respecting hero...' clause should apply".
But I still think your suggestions that becoming an initiate is "outside of the plot" or that "If you want to play such an oddball character, just do it" is prejudging what constitutes the game plot. In TV Analogy terms, if we are playing out an "Adventure Series" then it probaly isn't important, but if we are playing a "Soap Opera" then the success or failure of a character to initiate might be a major plot point against which the Lunar Invasion of Sartar is just background flavour. I think the game *system* should be able to answer the question "How hard is it to become an initiate" even if in any particular instance of the game we might choose to say "regardless of the rules, that is not an area we wish to focus on, so we will treat it as an automatic success / a costly success / an automatic failure / just ignore it altogether as appropriate.
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