Stick a paper clip or a spare connector into the plug to get the probe on it (obviously with the plug removed) to test the continuity. Yes, you can crimp 2 wires into the same pin if they are smaller gauge or you can solder the 2 together and a short length as a pigtail into the connector instead.
The switch test for system 7 is nice in that it will show all closed switches; do you get all 3 closed or the right most is open? Try taking the 3 balls out and put 2 in the upper lock trough, and the 3rd in the shooter lane - you should be able to start a game from there.
Some of the early williams are funny in that they will not start a game if they see TOO many balls in too many places, not just not enough in the correct places. So if there were 4 switches closed (say the shooter lane, too) it wouldn't start either.