Thanks for working on this so we can streamline everything.
Firstly, spacing in YAML is everything, so it has to be 100% perfect. In your text, now the text lines are off. If you use the > and continue on next line, that line must be indented 2 spaces more than the key line.
Secondly, in the quest thing, you cannot at this time use more than one attribute for a test. It just doesn't work.
Thirdly, you are mixing up character and progress levels, and I'm sorry that I named both of it "level". One is meant to be something like a dungeon level. 5-8 for a quest is very high, no characters at this time are that level.
Progress works like this, yes. In your example, the quest would fail immediately, because there is no challenge with progress 0 (where it starts). And because after "entrance" it won't find another valid challenge - it gains 1 progress for completing "entrance" and it's then looking for a challenge with progress 1. It seems you had the right idea but mixed up the two different levels. If you substract 5 from all of your challenge levels, it might work until "Ogre". Then it adds 5 and looks for a challenge at level 12.
I didn't think it's so difficult. I probably need some much better documentation.
