Difficulty / Target Numbers
Two questions:
1) How do you decide how difficult something will be?
2) If you were given absolute discretion in setting task/challenge difficulty, what could incentivize you to choose something difficult and challenging?
Difficulty / Target Numbers
Published
Lone Wolf Roleplaying 
Blades in the Dark handles this nicely with a two part system.
Action Rolls:
https://bladesinthedark.com/action-roll
Effect:
https://bladesinthedark.com/effect
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randomly, it’s fast and with no bias, and the difficulty is always balanced to the power level of the player character.
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1) I go by the examples in the rulebook for the most part. Once I have a feel for the system, this all becomes instinctive, so I can wing it pretty much without having to look them up. And since I want soloing an RPG to feel as much like playing a non-solo game as possible, I just treat it as I would if I were DMing for other players. However…
2) …if the game is too easy and my PCs seldom fail their skill rolls, it gets really boring really fast. So when in doubt, I skew things towards the harder end of the difficulty scale much more than I ever would when DMing for others. My solo games are littered with dead PCs, my social games hardly at all. If they weren’t, I’d feel sort of like I were cheating.
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