I did another playthrough were I would always choose the lines that support Kenny, his family, his plans, etc. Helped duck, stood up to Lilly and Larry, fed his family and left Lilly behind like he asked. Gave him the courage to help his son move on which helped him do the same to the boy in the attic.
At the very end when no one else would come with me; the speech he gave me about how I always had his back even when he wasn't sure he was right, how I've been a true friend and that Clem and I are family to him and he'd stay with us to the very end pulled my heart strings. He even gave Christa and Omid the boat if we're not back by nightfall, his entire plan and reason to come here and he gives it up for Clem and I. He's a true friend if you can just understand the guy and forgive his bigger problems.