The thing that grates is that they could have spent 3 minutes showing Dean applying for that job or even getting the job (glad was wrong and it wasn't a will), still hunting a bit, and then telling Sam he's quitting hunting, but let's take this one last case. And then he dies. To me that would have been truly tragic. Show us a time jump like 4 months later or something so we could see Dean seeking a new life, caring for the pooch, grieving Cas or trying to get him out of the Empty, and then accepting he isn't coming back. Show Sam grieving Eileen or having a long distance relationship with her. To me that would have had a much more tragic punch and would have been a much bigger FU to Chuck.
Because Dean had so much more character development, than this finale implies.
I'm still smad!