Ok, put your phone in your pocket, with the jack facing upwards. Now put your hand in your pocket. Pull out your phone without rotating it in your hand. The phone is now upside down. Hence jack on the bottom of the new ones results in phone being the right way up when you pull it out of your pocket.
Time out of pocket with headphones in, seconds.
Time in pocket hours, need longer cable, and I can't see any reason for it.
Remains flipping the phone upside down to go in, then flipping it when you pull it out. Far more rotating than at top.