I didn’t get the impression that Luke had such a strategy in mind based on his interactions with Rey. If anything, during their time together he should have been pleased that his plan has worked so well, and that another powerful source of light has arisen in the galaxy to challenge Snoke and Kylo. If Luke had simply said in the Jedi Tree that the entire religion was fatally flawed, they could have gotten past their antagonism and into a more interesting and rewarding track. Luke could have realized what Rey wanted and said ‘I won’t teach you the Jedi ways, but I can be a mentor and a friend.’ Then when Rey dives into her dark interludes with Kylo the inevitable fallout would be sharper for her growing friendship with the former Jedi.
Apparently the line, “It’s time for the Jedi to end” was originally a longer one, and I sort of think it may have given more context to Luke’s position.
I mean I think Luke’s perspective is implied by a lot of what he says. In his conversation with Rey about Jedi hubris, the rise of Sidious and Vader and then the eventual fall of Ben Solo, you can see that he is trying to get her to understand the cycle of good and evil.
He does want Rey to become something different, which is why he explains to her what the Force is, and how one does not have to be a Jedi to serve the light.
I think Rey continues to question Luke because she has heard the tales of the Jedi, and believe in what they represent. If she had never heard of a Jedi, maybe she wouldn’t have disagreed with Luke as much.
Maybe if Luke had lines being more direct, mentioning an actual “cycle” or telling Rey she could be something different, it would have been made clearer. I do feel like he was reluctant to train her partly because the line between teaching her about the Force and teaching her how to be a Jedi is thin, and if he taught her too much then the cycle would just start again. It isn’t until towards the end of the film that he believes that taking the lessons from the past and trying to learn from them is better than just completely starting over, he gets that hope back.
I think the the shadow discussion from my previous post carries over to this. The Jedi were concerned with purging/repressing their shadows, when they actually should’ve acknowledged their shadows, similar to how Luke acknowledges the dark side not being something inherently evil, like the Jedi thought. Fear and anger aren’t inherently evil emotions, but where evil comes in is how you act on those emotions.