Just to update-I went to dealership and they tested the 12v battery and it was bad. I guess the truck was going into some type of low power mode and shutting down the telematics stuff after a while. New 12v and no issues thus far.
Having the same issues since a few days ago.
So it seems after my update a few days ago, or maybe for no reason at all, my remote start and departure times have broken.
TLDR; seems like the truck is going into some kind of deep sleep and not responding to remote commands after a certain period...