Some interesting ideas! Depending on how you play with transitioning from shot for shot, you might also consider that there is a shot of Luke placing his hand on R2 from the second TFA teaser that doesn’t have that rain transition like the final film does. I could picture you using lines like, Kylo: The map… Han It’s just a piece… Kylo: You’ve seen it. During this you could show a shot of R2. Han: went looking for the first Jedi temple… [show the island, the tree] “He walked away from it all.” The Han dialogue could also tie into Kylo mentioning him during the interrogation as well.
I do worry about making the dream too elaborate which could make it feel out of place in the movie. I imagined something briefer, like a shot of the island and a shot of the tree. I also felt when you cut to this scene, you start with the dream first and we don’t see Rey until she wakes up suddenly. So something like, “Tell us all you know.” cut to black. Fade in on island. The simplest thing might be to start with her entering frame looking at the tree, and cutting when she is reaching for the books. Simple and mysterious.
You may just have to bounce this one around a little. I’ll have to think some more on it.