So I made it back over to the stealership (not the point of purchase but one located near my office). I took all 4 keys and printed this excerpt from the service manual:
PROGRAMMING THE WIN
CAUTION: Read all notes and cautions for programming procedures.
1. Connect a battery charger to the vehicle.
2. Connect the scan tool.
NOTE: Have the vehicle PIN readily available before running the routine
CAUTION: If the PCM and WIN are replaced at the same time, the PCM MUST be programmed before the WIN.
3. Select “ECU View.”
4. Select “WCM”.
5. Select “Miscellaneous Functions.”
6. Select "WIN Replaced".
7. Enter the PIN when prompted.
8. Cycle ignition key after the successful routine completion.
PROGRAMMING IGNITION KEYS TO THE WIN
CAUTION: Read all notes and cautions for programming procedures.
1. Connect a battery charger to the vehicle.
2. Connect the scan tool.
3. Have a unique vehicle PIN readily available before running the routine.
4. Ignition key should be in RUN position.
5. Select “ECU View”.
6. Select “WCM Wireless Control”.
7. Select “Miscellaneous Functions.”
8. Select “Program Ignition Keys or Key FOBs”, Start
9. Enter the PIN when prompted.
10. Verify the correct information.
11. Cycle ignition key after the successful routine completion.
NOTE: If the original keys do not successfully program to the new WIN after the proper procedures are followed correctly, programming new keys will be necessary.
NOTE: A maximum of eight keys can be learned by the WIN. Once a key is learned by a WIN, that key has acquired the Secret Key for that WIN and cannot be transferred to any other vehicle.
I now have 4 keys 2 with remote start.