I got it!!!
The drilling may have helped loosen it up a bit, but it wasn't getting me far. What finally did it for me was the PVC pipe and my shovel. A good analogy to what I done: PVC pipe = nail, shovel = hammer. I stuck the pipe in the small hole I managed to make under the sidewalk and beat it with a large shovel until it came out the other end. Considering how much fun I had I'm going to just route the system around by my sidewalk and continue it that way versus making a second tunnel that was an experience... ugh.
I may try my alternate plan (running tube in sidewalk crack with a cord protector over it) to get to my mailbox flowers, both sides are landscaped already and it would be a huge pain to dig, move plants, lift my rock beds up, etc. If it won't work then the heck with it I can water those myself.