When asked at the Manatee Library event if we could ever see Roland again he responded (full video below):
58:50 She’s talking about Roland from ‘the Dark Tower’, and all I can say is, the Dark Tower never really leaves. It’s kind of the binding force between a lot of these stories. And there’s a booking coming out in the fall of this year, a big collection of stories, called ‘The Bazaar of Bad Dreams’. There’s a story in there called “Ur”.”U”, “r”. It’s a revision of a story that was published in a limited, as a kindle ebook. A couple of years ago. But that’s a real, balls to the wall, Dark Tower story.
So Roland is still there, I guess.