... Can't tell if you're being facetious or not, but here's a sample trello board that mimics our workflow:

https://trello.com/b/TTAVI7Ny/ue4-roadmap

This is not a good fit for org-mode, despite what any number of org-mode zealots say.

I think from a casual user perspective, knowing how to do it ;-)

I'm not a casual user. The inline images functionality of org-mode sucks in comparison.