Great points. I’ve always thought the Jedi were wrong in some of their beliefs about the force, no attachments being one of them. I’ve always thought that if Yoda wouldn’t have told Anakin that he should let go of all the things he feared to lose, he may not have turned to the dark side.
It’s certainly possible Obiwan began to reject some of those beliefs, but A New Hope doesn’t seem to present Obiwan as someone who had a romantic relationship in the past or a child. But who knows? It would be interesting.
I think Rey is a Skywalker because if Luke is the last Jedi, then he’s rebuilding the Jedi Order from scratch. He realizes that love is important and becomes a father, never fearing that it’s a path to the dark side.