Thanks for the input everyone. I'll definitely try to minimize the amount of slack I have on the wires from now on, hopefully keeping enough length to be able to maneuver the pickguard without too much trouble. I'll also be more mindful of where I have the long lead from the jack and I already like to add some electrical tape over the shielding just to provide a little barrier just in case there is some contact.

I just thought I should see if I'm missing something since it's happened to me three times now where if I have the screws tight it won't work, but if I loosen the bottom screw off then I have sound.