Ok, I have pretty much ruled out it being a grounding issue... at least I think I have. And the issue has gotten worse.
I tightened the screws on the boards in the head, not too tight but nice and snug, and got no improvement. Then I saw a TNT amusements video where they showed using copper along side the board to ensure proper grounding. I figure it couldn't hurt, so I ordered some.
As I waited for delivery, play time got shorter and shorter until I couldn't play a single game without the flippers cutting out completely. I received the conductive copper tape today, and tried to replicate what TNT did on their video, no improvement.
I did notice one new thing though, I had the head open and when the flippers cut out I heard a click from inside the head. After some investigation I'm 99% sure it's coming from the solenoid driver board, and I'm 90% sure it's coming from this 'box':
WP_000017.jpg
Any ideas? What should I try next? Remember I can't solder worth %#!.