Pins 2 and 4 in the Crack are connected by a wire, yours are different by 50V, so they can't be.
Pins 7 and 9 are above pins 2 and 4, which also doesn't seem possible.
Pin 6 is showing DC voltage, so it's either not connected to the headphone jack, or there's a wiring issue at the headphone jack.
The Speedball readings don't match the terminals they wire to, so again, this is like the 2 and 4 being wired together but showing different voltages.
This is either a lot of mistakes, or a lot of solder joints that aren't solid.