I'm with you. I was hoping that he AirPods would have been $99 and that would probably help Apple realize economies of scale to make their profit.
In regards to the case, I see what you're after now and that makes sense. For some reason, I had thought you wanted to design a case that had an actual audio jack in it. My bad. What you mentioned seems completely doable. Two lightning ports would not take up near as much room. Considering that so many people put their phone in a mount in their car, I would think it would be paramount to have both lightning ports coming out the bottom vs one on the side, especially since a case needs to reach as broad of an audience as possible. Thoughts?