Maybe he wants to be surrounded by players that can help him win a title
Maybe he prefers living in a real metropolitan area like NY or Los Angeles vs. one built around Mickey Mouse.
Maybe he is losing his hearing from all the constant screaming by his enlightened head coach
Maybe he is tired of ownership constantly making all the wrong decisions
Maybe he just wants a change of pace.
Personally, If I was given a choice of places to live out of Los Angeles, NYC area, Boston, Dallas, Chicago, Miami and Orlando..I know what place would be at the bottom of the list. Orlando. That town does not offer a ton of culture. It is filled non stop with tourists. Most things close at 10pm. It is humid like hell and there is no ocean surrounding it. Culturally it is at the bottom of the list as well. The restaurants cannot hold a candle to the larger cities. Both of my grandparents lived in Florida and I have been to that state too many times to remember. My least favorite city was Orlando. It is my personal opinion but I can completely understand what is going through Dwight's mind.
Winning, better environment both within work and outside of work, Being able to choose his own destiny and at the end of the day, being happy. If he is not happy, he should not be forced to stay in a place that does not suit him. Being a King is Sandbox surrounded by no ocean is no different than being a Peasant in a Kingdom surrounded by gold- both parties are miserable in the end.