I "like" this episode. It's hard to say "like" with it though, because it's got issues. But I like that the show actually wasn't afraid to do an episode like this. It was on the WB network at the time, so can't fully compare it with the CW. Everyone breathed a sigh of relief when the CW agreed to keep Supernatural when they took over the network and it's shows. It has never quite fit the type of show the CW is known for, and so has had a lot of times it was at risk of being cancelled over the years.
Dean does act like a ladies man, and I'm sure he isn't shy about hooking up, when he can. But it's nice to know that he has no problem with an actual relationship if it can happen, but if it can't then have some fun.
I agree with you about the actress playing Cassie. I've seen her in other things, but I can't recall any details. Doing a romantic relationship with another actor you've just met would be difficult.
I get what you were trying to say about the Mayor, and agree. He may have helped Cassie's father, and not liked what Cyrus was doing, but he that doesn't mean that he didn't have some biases. I think he's typical of many people still today.