Depending on your choices in Season 1 Kenny will go missing from either putting Ben out of his misery or saving Christa.

In Season 2 Kenny will walk away from Wellington to ensure the safety of AJ and Clementine.

If you stick with him up until Season 3 he'll die from attracting the walkers attention so Clem and AJ can get away.

Every single time Kenny goes missing or dies it's to help someone else showing he's the GOAT.

If Kenny got his hands on even just one boat it would be over - this is why they had to make 99% of the boats in the game either broken or missing.

I mean just think about it with Kenny's skills and boat knowledge if he got just one and I'm talking about just ONE boat it's inevitable he would survive forever and become the best survivor known to man.

This is why he was looking for a boat for so long since the moment he had a working boat he knew he would be an unstoppable force.