A suggestion for the montage:

Have you ever watched the Sandlot? You could have a voice-over of an older Luke keeping a journal entry (call-back to the journal of the whills) to upload into R2. Have footage from the previous films showing the characters, and whenever a character's "fate" is done being revealed by Luke, the image of the character sort of vanishes into thin air.

"You ready R2? All right. Journal entry of Luke Skywalker. 40 ABY." Maybe start off with something like that.

Show Han cleaning the Falcon in preparation for its take-off from Mos Eisely: and when Luke is finished saying "last we heard is that he had a run-in with bounty hunters. We haven't been in contact with him for years." have the figure of Han gradually disappear, leaving the Falcon alone in the docking bay.

That's one example.