In some ways, the Skywalker bloodline always met in failure.
Anakin fell into confliction against the ways that the Jedi was teaching/ruling, while Palpatine was sharing that the dark side isn't always what it is; and when the time came, fell from the path of light. Even with his "redemption", he died the moment he first was put on the mask.
Luke, in some ways; isn't that far off from the tree. He nearly fell at the final battle of the Empire, and even when training Ben; nearly fell to killing his own nephew. And while yes, he did stop; he in some ways; fails as a teacher. For both Ben, and Rey; as he didn't exactly have what was needed. We can praise his farewell all we want, but that doesn't entirely change that he is extremely flawed.
Admittedly, the one that hasn't had this issue; is Leia.