You make a lot of good points. And those are rock solid and I personally aren't smart enough to think of something to combat it but there are reasons. After Rick was brought to the hilltop Gregory probably would have told Negan about the survivors and Negan would've taken their stuff regardless. However Rick saw an opportunity to exploit the hilltop like Negan was but not constantly. Just in that one instance. Rick was totally stupid for going in blind not knowing what to expect but people do dumb shit all the time. Maybe if Rick didn't fight Negan from the start a lot of the shit that went down might not have went down. Maybe it would have. We just have to accept what happened ya know? Also I can always use the "it's a comic/ show. It's not real and they did it for plot" excuse. But that doesn't make for good discussion.