Insurgentes was a risk. It was his first solo album, and his main influences and sounds on the album were more obscure and experimental (noise/drone for example). I don't think either GfD or Raven are risks, because both are progressive rock albums, and most of SW's fanbase are already familiar with that genre. Even PT has a lot of 70's prog rock over some of their albums (and songs), so it was more of a natural extension of that, compared to Insurgentes which was more a combination of his obscure projects (Bass Communion and IEM) mixed with some PT-ness.
I think though what separates them is that Grace was the first album after PT sort of being disbanded, and by the time Raven came out, I think most people had already accepted that his solo project would be his main project from now on.