Just to follow up it took two and half hours to get my bag back. Apparently the original pull order was never transferred over properly to the ramp, according to the supervisor in T5 BO. So when I went to check back in at the two hours mark, he took over my case and I got my bag 30 minutes afterwards.

Not ideal, but I was headed to the parks and wouldn't be anywhere in the vicinity of the airport; so it just seemed like the lesser of two evils. The system just seems dysfunctional.

Side note on the ride back to T5 from the Eagle's Nest, a Air Canada 7M8 pushed right in front of us, blocking the vehicle path and the shuttle driver said "f@#@" under his breath. That made me chuckle; got to imagine he was almost at the end of his shift.