Not exactly analogous but if you are looking for some inspiration, there are some interesting data sets to browse though on data.gov[0], and innocentive[1] has "challenges" in a variety of areas.
Sure. Browse Upwork or Freelancer.com and see what the buyers are asking for. They may be delusional in terms of what they want to pay, but at least those are examples of needs people have that they are willing to spend money on.
[0]: https://www.data.gov
[1]: https://www.innocentive.com/ar/challenge/browse