Okay so I haven't been able to post until now since my bad sleep schedule and I was out this entire evening. Most of my thoughts have already been shared - except I disagree with the assumptions that the Jester did a stress relief on the Jester.
First of all, it was stated in the OP that we start at 0 stress and we go up to 100 before triggering an event then dying. The info panel at the bottom said "+15" not "-15" so I'm inclined to believe that the Grave Robber's stress had gone up. Additionally, the flavour text mentioned that the Jester relieved the Man-at-arms from whatever happened, and not the Grave Robber. Furthermore, going by the Jester's flavour text in that section, it seemed he negated whatever happened - rather than relieving stress specifically?
edit: Since it hasn't been clarified in the OP what any roles do, perchance we should make a public list as we find things out?
For example:
Vvul: Head cultist, recruits peeps
->When I get more time, and the motivation to do so, I can go back to TDD1 and list out what the recurring roles from that game do in this game? Or do we want to leave this info more secret so the different evils/terrors are more in the dark (ha! get it?) as well as potentially spreading misinformation based off what he had previously and throwing other heroes off? :/