I think its the exact opposite. When you're in a crisis situation, there are a select few who can stand up and take charge. But the vast majority of people panic, shut down, and wait for someone to come save them. I think they've done a really good job of showing how Negan selects people that he thinks are very valuable, then gives them the good life to keep them loyal. If you have a nice little savior apartment with working ipods and a menu of food to eat, you can probably stomach a lot of the other crap that goes on. Remember the alternative is zombie duty and escape means zero shelter or resources on the road with zombies and other groups popping up to kill you at all times of the day. That is assuming Negan doesn't send someone to hunt you down first.
As for Dwight, he seems to get bullied up and abused by Negan a lot more than the other guys. I think he was willing to do just about anything because he loved his wife and wanted to keep her alive. Negan knew that and made Dwight his plaything, but should be smart enough to realize that relationship has changed. With Dwight's wife gone, he's got nothing left to lose, so why not betray Negan and help Rick take him down? It's not about the cut of his jib, it's about revenge. Yeah, he could probably just pull a gun and kill Negan at some point too, but then some other prick would just take his spot. I think he wants the whole system taken down, especially seeing how Rick's group works together. Plus he's clearly in love with Daryl.
There's another interesting thing to note about Negan: misguided and cruel as he is, there is a level of restraint and efficiency to how he brings people in line. Yeah, he kills people pretty brutally from time to time, but it always relates to keeping the rest of the group in line. He had Alexandria in a position to kill them all, but he didn't. He's given Rick half a dozen chances and only with this last speech of defiance did Negan decide to finally end Rick and Carl. Not saying he's a good guy by any means, but there might be something more there than just being a sadistic jerk dictator.