Tick anything you already have, in any order. Quests unlock once this is done.
Most cities have permitted walls where painting is welcome and you can take your time. Painting anything else is criminal damage, whatever it looks like afterwards.
Find a legal graffiti wall2 things left above. Quests are real things you go and do, so they only make sense once you have what you need.
First one waiting: Fill a sketchbook page with one word in ten styles