First, how do you make roleplaying games something that anyone can pick up and play for as much or as little time as they like – for example, at a party where people who aren’t already gamers are walking up and looking to experience this new thing without having to commit their whole evening to something they’re not sure they’ll be into? I feel like this is an OSR question because one of the hallmarks of the RPGs of the original era was that they enabled a situation where stoners with Frodo Lives buttons in a college dorm, or new recruits on a military base, or imaginative kids at a school game club would be able to walk up, create a character, and get hooked. And revivalist things like the Tower of Gygax are better enabled to do this than anything else I know about.
Second, how do you reconcile delivering an instant hit of RPG goodness to newbies with the contradictory goal of satisfying the “this campaign could be your life” promise of the neverending story? James has talked about how, even in a nominally open-table game like the White Sandbox, the mass of information an ongoing storyline accumulates can be off-putting. What structure will keep an enlivening churn happening between new players who want to be enthralled by the way their choices produce immediate results and old ones who want to keep on getting deeper into an exploration of the consequences of choices they made many sessions back in their collective memory?