Was there an objective reality that existed whether or not we could ever observe it?
Were there laws that restored strict causality to phenomena that seemed inherently random?
Was everything in the universe predetermined?
When do political parties start being a bad idea?
Why don't we want the government controlling the internet but we're okay with them controlling our education system?
How is it that outcomes can be likely and not happen and outcomes can be unlikely and still happen?
Is a democracy possible in the information age? Or has social media and technology changed the way humans function in a "democracy" and policy hasn't caught up yet?
Where do jokes come from?
How many people do I admire that are actually miserable?
Which people know what the right answers are, but no one listens to because they either 1. Don't look the part 2. Don't act like the part 3. Don't talk like the part?
Is there really a difference between a more-disciplined person and a less-disciplined person, or do they just experience their temptations in different ways?
Why isn't anyone building something like the Statue of Liberty, The Eiffel Tower, or The Great Bridge anymore? The coolest thing in recent years may be modern looking skyscrapers.
How is it some things existed in the past but there's no record of them in the present (online)?
There are a certain set of questions/problems that every person is faced with: how to choose a spouse, how to pick a career (and when to leave the one you're in), how to deal with difficult family members, how to deal with losing someone you love, how to enjoy life outside of work, and many more. Why is there no Thesis on Life or an almanack that answers these questions? Tim Ferris's Tribe of Mentors is the closest thing I'm aware of and it's still a long way of. This would be a really, really fun project to work on.