did another playthrough, he used a spyglass on a gun with mostly live rounds, used handcuffs, then shot himself with a live round.
Seems like the devs aimed for the best unpredictability factor to be present thus randomizing the dealer's outcomes, the AI seems to be lacking at times especially when the dealer is on it's last life charge but it actually looked like the dealer has decided to take the L when he had no tools left and the life charges were looked in.