Jeff,
I probably have this theory wrong, but it's my understanding that ignition wires are engineered with some resistance which allows the voltage to build slightly which results in a stronger spark. This also happens when the voltage reaches the electrode on the plug...it builds until it has sufficient strength to jump the gap.
Because you are using solid core wires, they might not have enough resistance to allow the voltage to reach a adequate level for the inductive pickup to read.
I know the inductive pickup on my timing light has a big warning label on it not to drop or slam it...it's rather delicate. Could your pickup be screwed up!
When you pull the plug wire and the light works, I think you are creating artificial resistance in the wire and the pickup and sense it and the light triggers.
I might be all wet on this theory...lets see what the guru's have to add.
Stuart