Has to be:
not dependent purely on luck
not cause inconvenience for people
be safe and legal
I will give bounty proportional to my (interest)+(chance of attempting it in the future) capped by 50 mana. The challenge should be at least theoretically manageable ("fly to moon" is not a good challenge, as it would require all my lifetime resources and insanity of luck).
Here are couple examples of what I consider challenge:
1) German film "100 Things" represents one to live with using limited things. But this one is hard.
2) Generating a random letter and not using it in verbal speech for a week.
3) I created a market about "No lazy challenge" (link at the end).
I plan to make it a series in my life. When I complete or fail one challenge I will pick a new one (potentially one of presented in the comments).
I will add mana periodically.