Thank you for the thoughtful feedback Thomas!
I agree that the first contribution/feeling of belonging is an important step that needs attention. I will definitely be championing a collective effort towards solving these types of problems in the first round of Arrow Compass priorities.
I also think this could be something great for me to work on as part of my proposed Docs Maintainer and Improver role. Bounty board will definitely get some love and we can work out some sort of system where perhaps a new contributor gets something (token or role on discord etc). I recently had a good onboarding experience with https://3dos.io/ where new users could earn token right away by completing some tasks (engaging with our socials, joining discord, introduction, making first PR - even just adding to contributors.md). Having a user profile with my tokens earned in top right corner was a pretty nice experience!