Tick anything you already have, in any order. Quests unlock once this is done.
Smooth paper matters more than the pen. Normal printer paper shreds a brush tip within a page, and cheap laser paper fixes it for a couple of dollars.
One thing left above. Quests are real things you go and do, so they only make sense once you have what you need.
First one waiting: Try faux calligraphy with a pen you already own