Hey, Nespy! Thanks for reaching out, we're happy you're interested in Wonderfall and we hope it's a nice introduction for hexcrawls! Let's get you some answers:
1 - Exactly! These tables are there to use as you please - so roll as many times as you want to create cool stuff! They're supposed to work as building blocks, supplying ideas to help you craft your story! Try to think of fun ways to combine and interpret them - what do they make you think of?
2 - Either way works, really, so it's up to you! You can head to a location knowing what you'll need to solve beforehand, or find out what the problem is once you get there. Whatever works best for your story - we like to use a little bit of both :) You can also always use the previous tables (for People, Encounters and Locations) to generate interesting things to interact with and frame your Problems.
3 - Quests come up whenever you enter a City! The world is trying to heal and there's always trouble to solve - so whenever you enter a City (be it to check back once you've solved a Quest, or if the current Quest brought you somewhere new), you can roll for People, Encounters and Quests again to find out what your new mission is going to be! You can even work on multiple Quests at once if you feel like it!
Let us know if there's anything else we can help you with, there are no dumb questions as far as we're concerned! We hope you have fun helping heal the world!