We have always tended toward the extremes, and favor the early side but we have done a super late arrival once, too, and it worked out well.
We have enjoyed trying to get out on the first flight of the day, and because DW is a notorious worrier, we would be at the airport at 5 for a 7 am flight, which meant leaving home by 3:30. When we arrive early we have done different things, but most often we just tour resorts or go to Disney Springs. Our long standing tradition is dinner at Raglan Road on arrival day and buying a customized ornament for our Christmas tree. However, since we always go for at least 7 park days, at that point it is so inexpensive to add one more day that we have occasionally done a half park day at a very casual pace and still gone to DS for our dinner and shopping.
On our most recent trip in March, though, we took a late flight out. A part of me genuinely cringed at the idea of paying for the hotel on a day when we literally checked in after midnight, but at the same time it was a fuller night of sleep than if we had taken the 7 am flight and then we casually had breakfast and still went out to DS.
This will be a bit hypocritical as our November trip we are, once again, arriving late (11 pm) but given travel woes lately I would probably say to take the earlier flight. That is part of what we liked about earlier flights when we opted for that timeframe. We thankfully did not have a cancellation in March but there was a delay, though at that time it was due to traffic near the airport as there is a ton of construction going on there that is just maddening.