You have a whole lot of cold joints, which will cause you problems.
You need to ensure that:
1) You have enough flux in play
2) You have your iron hot enough, but not too hot
3) You get both the pin and the pad hot enough, quickly, so that:
4) solder flows down the pin, across the pad, through the plated through-hole...
5) and you can remove the heat so that you don't start burning stuff, lifting pads, etc.
You may help your situation by getting a flux pen and using it to add flux before
you try and add solder - add the flux, add the heat, then add the solder, or in most
of your cases, simply add the flux, then add the heat - you probably already have
sufficient solder. There shouldn't be any of the pad left visible without solder if
you're doing it right because the solder will flow right across the hot pad.
While you need to address that in order to get reliable operation, it shouldn't be
causing the short-circuit to GND on the USB 5v that you're experiencing. I am
still suspicious of your TRRS cable. Have you checked for shorts in that? Have
you checked with your multimeter for shorts from power to ground when it is
plugged in?
