I think the 'how will I charge and listen at the same time while I drive' problem is easily solved and is on most new cars already.
Any ****ty old car with an AUX port and a 12V can be 'upgraded' to Bluetooth with a $20-40 hands free kit.
e.g.
https://www.amazon.com/dp/B00GJFGE0K
From what I've seen any newer car that has a USB port not only charges but is able to play music through the stereo as well.
Wireless sound quality will improve, perhaps someone will even develop a nice cheap pocket Bluetooth DAC so you no longer have to physically tether your phone to your headphones to begin with.