Re: questions about jobs for your hero
1) I would suppose it would depend whether you were wearing that armor at the time or not.
2) If the character is a PC that the player cares about, I would strongly suggest that the GM have job events be actual situations that get played out, not "roll or take 4d damage". That can turn them into something interesting and meaningful, and give the players a role in determining what happens in a much fairer and more satisfying way.
I'd suggest developing the job rolls so that events happen more frequently but have different types and severity that mean you play out different types of on-the-job events with different possible risks, rewards, and developments.
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