Tick anything you already have, in any order. Quests unlock once this is done.
A secondhand bike serviced at a local shop costs a fraction of a new one and rides better than a cheap new one. Lights are not optional once it gets dark.
2 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: Ride ten kilometres comfortably