" I have all proper test equipment"
What is this equipment that you have? If I'm reading this correctly, your saying that you have the "test equipment" but, don't know how to use it?
You have to turn on the outside breaker to get power to the inside breaker.
After reading this four times, I have come to the conclusion that you want to determine why your not getting power inside versus "testing a breaker".
Turn on the outside breaker and check the black wire to ground and the red wire to ground on both the line and load side of the breaker. Then check the black wire to white wire and check the red wire to white wire, on both the line and load side of the breaker.
Then do the same on the inside panel box.