Hey Guys... just a quick update on this.
1. I ordered two aftermarket (but identical looking) keys with remote buttons off of Amazon for like $35 Canadian.
2. I stuck my original programmed transmitter key near the ignition and tried to use one of my non-programmed (but cut) keys, but it just didn't work no matter where I put the programmed key including touching the two keys together. The truck would start for a few seconds and then die.
3. A locksmith was able to program one of the keys with no issue and suggested that the dealer just didn't know what they were doing.
4. I was able to program the third key myself using the truck itself using the original key and the key I had programmed at the locksmith.
Thanks for the advice!