Wait for 40 more years, and ask 2 generations of kid grow up today what is 3.5mm jack, they will remove their wireless headset and ask what did you said?
Like I said, change is the only constant.
Wireless audio will improve, specially when iPhone come out without a 3.5mm, which will push a lot $$$$ oppotunity for 3rd party wireless headset. No wire will be cool and is the future.
Just like you said, hard to imaging lightning connector on another end, but you don't have to imaging wireless headset, it is here already.