Very admirable approach Cavewizard, I think it is great that you have grappled with this type of self initiatory process.

While I can appreciate the level of seriousness that your body modification represents in terms of your journey, I wonder if your reasons for this path are for the initiation you speak of. There can be no doubt that discipline carried out upon the phsysical can have enormous transformative effects which can reveal aspects of the self and its relationship to the universe - still the mental and emotional aspects of being require similar ordeals.
Tattoos, Piercings, brandings and other body mod techniques can be ritualized toward inititory gnosis, but perhaps having mastered that one could move into other equally important areas of the self. [Caveat: I bring these points up as hypothetical and for the sake of the discussion, I do not mean to imply that you need work in these areas - how could I know?].

When you say 'stumbling' what do you mean? What aspect of things represent that stumbling block? Those 'blocks' are key to understanding the crux of the situation and point the way to issues worth considering.

Self initiation can be tough since it requires a conscious and careful attention to the threshold you are crossing - it may be difficult to recognize the habit patterns which can be quite obvious to someone outside and [ in the case of a good initiator] objective of you. Nonetheless it is a laudable activity and can prepare one for further initiations.

Our 'culture' indeed has problems in terms of initiation simply because it requires a deep look into one's personal abyss - an act few are willing to negotiate let alone pass through.