What kills me about wireless is when I need to switch sources. E.g. from my work laptop to my phone and vice versa. Or from my work laptop to my personal laptop.
Perhaps Airpods do a better job here, but my experience with Bose and Sony wireless headphones has been terrible on switching sources... I have to manually unpair from device A and repair with device B. In the case of Bose this handoff is mediated by an iOS app that seems to crap out 50% of the time. It often takes several minutes to get everything working as it should. This does not feel like a $350 UX.
It makes me rage when I think of the ease and speed I had in the past with wired headphones that can be instantly unplugged from A and plugged into B quickly with 100% reliability.