Couple things about Kayn
So I've been powering through as many games as Kayn recently trying to get my quest done and I've noticed some things that poke out at me or feel weird.
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Passive - This thing is a QoL nightmare. Having your choice of kit so heavily restricted based on what you can do as a jungler is really unfortunate, and you can feel shoehorned into the wrong pick sometimes. Especially when you're looking for a specific upgrade. Forcing ganks on bad lanes as a jungler instead of helping out the team is REALLY poor mechanics. Furthermore if you're a laner that choice is effectively not even a choice. If top and mid lane is melee you are essentially going demon, and if it's ranged you're going shadow. There's an illusion of choice with too many variables and while an interesting idea I think there's a much better way to have gone about this. Also the visual for the meter sucks.
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EDIT Upon further testing it does work with chilling smite, it's entirely possible that I had noticed something else during the games, but chilling smite does activate Kayn's Ultimate.
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Ultimate healing has a weird delay on it. When you break the ultimate from Kayn's demon form, there's a short delay from when the damage is done and when the healing is applied, enough that damage over time effects applied before using the ultimate will kill you before you get the healing. As far as I am aware, there's no visual projectiles that have to reach you like some other champions, so the delay just feels and seems odd.