I want Dwight to stay. But let's look at it from his perspective and examine why he might want to leave... why he maybe should leave.
First, let's assume that Dwight's main goal is to win... and to win a lot. Obviously the money is already there. On top of that, he lives in a warm weather state, with no state income tax and is a tremendously popular, perennial all star. So it has to be about more than whether or not to stay in Orlando. This is about competing with teams that have multiple pieces.
With that said, ask yourself this: can the Magic seriously compete with Miami and OKC over the next decade? Can they compete with the multiple star teams?
No, not right now.
So if I'm in Dwight's shoes... I'm looking at the teammates. Does this organization have the means to build a serious contender, (for example: can they attract another star player)?
In New Jersey he could player alongside Deron Williams, in LA he could play with Kobe and in Dallas he could play with Dirk. We all know that. So what about Orlando?
And this might be why Dwight should leave. He has to ask himself: do I have the ability to be the guy who brings in another player?
Does he have the alpha male mentality when it comes to selling his team? Why isn't he reaching out to guys like Deron and saying "come here?" If he is, why hasn't there been more success with that outreach?
Is it possible that Dwight just doesn't have the personality to bring others in? Is it possible that he needs to go and piggy back with what someone else is already doing?
I know we don't have a lot of room to manuever in free agency right now. But that can always change with creative trades that dump contracts. So why isn't Dwight saying to the team: "Let's do this. Free up space... and give me the chance to get someone here?"
It's a lack of leadership. Plain and simple. Dwight is a great center (best in the NBA right now), a decent man, and will most likely end up in the Hall of Fame. But he doesn't have the leadership to get this done.
So ultimately that might be why he should leave. He's a great guy and I wish him well, but I think he needs to play second fiddle to a Kobe, a Dirk or maybe a Derrick Rose. If he can't be the guy that people want to come and play with, then it makes all the sense in the world to go hook up with another team where he can be a piece of the puzzle.