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I'd find it very odd that Yozora meets Sora by chance while taking a nap in his car, especially when everyone in Sora's reality is looking for him including Kairi who voluntarily placed herself in a coma to investigate the boundary between sleep and death. It's more likely the trials he referred to gave him that power, but that isn't a power that can be obtained from the reapers game.Chirithy: "The edges of sleep and death touch, and one can't help but the occasional crossover."
Yozora contacted Sora through sleep/dreams, which is why both versions end with Yozora waking up after the battle.
I had another thought that keyblade wielders could sort of be thought of as the "angels" in TWEWY. Even Joshua was surprised to see Riku show up in DDD which would seem to indicate that Riku (as a keyblade wielder) has some power greater than a composer - which are only briefly mentioned in TWEWY as angels. As we don't actually know what the roles of keyblade wielders are I think it would be a cool story concept and an awesome way to link KH to TWEWY. If it turns out Yozora is on par with an arch angel in TWEWY it would make some sense that he could cross over planes and find Sora as well.
Funny enough, the "Producer" in TWEWY is an angel sent to Shibuya allowed to communicate with the people there, but forbidden from revealing his identity as an "angel". This is sort of reminiscent of KH1 when Sora is repeatedly told by donald and goofy not to reveal his identity as a keyblade wielder from another world because it would mess with the world order.
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