He’s Actually Crossed Paths With Luke Already

We’ve seen in the trailers that Obi-Wan is watching over the young Luke from afar, yes, but we’ve already had several tales of Obi-Wan encountering Luke in the current Star Wars canon at this point in time, thanks to both A New Hope anthology collection From a Certain Point of View, and the Marvel Star Wars comic’s initial volume, which included several tales from Obi-Wan’s journal that recounted such details.
When Luke was just three, Obi-Wan rushed to the aid of the Lars homestead when it was attacked by roaming bandits—only to be chased off by Owen Lars for interfering. A few years later, Obi-Wan found himself coming to the aid of Luke once again, even if the young boy didn’t know it, protecting him from the thugs of Jabba the Hutt during a water drought.