This could work out pretty well. I remember reading somewhere (can't find the article) that Brian Eno works with artists this way as a producer, creating artificial constraints to expand their creativity. Would be interesting to see how this affects the startup process where optionality can be overwhelming.

I think this is a super interesting idea. It feels like the natural progression of this would be a set of UI tools to rest on top of JIRA / Trello, or a new task management platform of its own. Basically, a way to create the "gameplay" automatically in the UI

D&D is role playing, and role playing is interactive learning.

multi user dungeons were used as the basis for the first interactive online learning systems.

so most certainly this idea is a great fit, whether it's online or offline.