Regarding Chester, he's what's called a "heel" in wrestling terms. His character is designed to be hated. With that being said, I've always loved the heels in wrasslin' and Chester is no exception. He's done almost flawlessly. The perfect heel wraps you in and gets you emotionally involved and then gives a reason for the hate. The more involved you were the more you hate him in the end. I think he does just enough to show he's a villain while most of his existence is just pulling you in deeper. I couldn't stop visiting just to see if he had new dialogue.
I hate Chester personally but simultaneously love the character if that makes sense. The game is much richer with. Plus his coat + bloated head and almost any gauntlets and leggings makes a perfect Skarekrow outfit.