>* Having to charge them is a PITA

The equivalent PTIA for wired would be having to untangle them everytime you want to use them.

>* Having to pair them is a PITA

How many devices do you have that this is an issue? This is an issue that pops up a few times a year, at most.

>* Having more points of failure is a PITA

It's unclear which has more PoF. Wires can break, not to mention randomly catch on stuff and sending your phone flying.