My experience with USB in general is it's a PITA if you need to insert / remove on regular basis. The sharp edges scratch at the plastic, and you typically always try to insert it at the wrong angle first try, and so need to play the USB dance of switching back and forth until it finds its way in. Its impossible to do while in your pocket, which is where the jack really comes into its own.
One downside compared to micro-usb in my experience was having my macbook stop charging after (apparently) using the wrong usb-C adapter. I don't think I ever worried about which actual adapter I used for a micro-usb device, but I guess you have to be more careful which usb-c chargers you use... another example: http://arstechnica.com/gadgets/2016/02/google-engineer-finds... )
This won't help with the connector wearing out, and when there's only one connector for charging and headphones (and everything else), it will wear out more quickly. The USB and Thunderbolt ports on my laptop are already getting flaky, and it has been a mere 2 years.
My experience with USB in general is it's a PITA if you need to insert / remove on regular basis. The sharp edges scratch at the plastic, and you typically always try to insert it at the wrong angle first try, and so need to play the USB dance of switching back and forth until it finds its way in. Its impossible to do while in your pocket, which is where the jack really comes into its own.