All of Kenny's decisions are about taking risks. A lot of them unnecessary or not that thought out. "We break the lock and see what they're hiding. If those farmers give us trouble we take em' out" or something like that. Let's not forget rushing to rescue his family without even grabbing a weapon or looking for the other brother. Some are sensible risks like we have to leave our safe haven otherwise we starve. Lilly is all about playing it safe. She doesn't want any new people because they are unknowns and extra mouths to feed. She doesn't want to risk leaving a place they know is safe to try to find someplace with more food that might not exist. When given enough suspicions about the farm, she suggests just leaving without snooping around or getting dinner. She also doesn't want to loot the car because it might not be abandoned and she doesn't want to risk fucking up somebody's life. The only time they are reversed is with Larry for obvious reasons. Just my two cents.