Well hits from people recently mean they have poor body condition Billy won't be taking a shot from say a dozen knives from Hassan of the Cursed arm too well with an endurance of E for example. And he was a trained outlaw. 

If a servant dies in a singularity that's fine but they can't be re summoned until people are returned to Chaldea. [@Lonewolf685] I think made a good suggestion by making tweaks to the yuri pirates to make them less summer fan service style.