Since I'm technically acting as both initiator and abettor, would I have to roll to potentially damage myself, or would it be a non-issue since I'm not really there on the other side of my flanking target? One could argue that I'm both there and not there at the same time; Schrödinger's Flanker, if you would.
They don't work together.
The FAQ for counting as your own ally says:
Ally: Do you count as your own ally?
You count as your own ally unless otherwise stated or if doing so would make no sense or be impossible. Thus, "your allies" almost always means the same as "you and your allies."
Given that Wild Flanking says:
When you are flanking an opponent with an ally who also possesses this feat, you can throw yourself into your attacks in such a way that your opponent takes extra damage, at the risk of these attacks striking your ally as well. When you choose to use this feat, check the results of your attack roll against both your opponent’s AC and your ally’s AC. If you hit your opponent, you deal bonus damage as though you were using Power Attack. If you hit your ally, the ally takes no damage from your attack except this bonus damage. It is possible to hit both your enemy and your abettor with one attack. Extra damage from this feat stacks with Power Attack.
It makes no sense that you attack yourself when you use this feat (you can only be in one place after all). This means that it makes no sense for you to count as your own ally in this situation, therefore you can't benefit from both feats*.
*: Unless you have an ally with wild flanking who's already flanking the creature for you.