We almost always take a late flight on departure day. For each individual though it depends on what time of year you are there, where you're staying, and where you're going. We almost never do WDW in the heat of summer, so storms are less of an issue. Late flights during heat of summer have the highest chance of disruption.
For our upcoming mid-September trip we have a flight out at 5:15pm. We are flying back to Baltimore. (Even though we live in Philly. BWI is only 45 minutes further away than Philly's airport time wise. We
HATE PHL and drive the extra hour for a better airport and more flight options.) Our last day at Beach Club is set up as a TBD...
- Wake up time is dependent on when we get to bed the night before.
- Choice 1 is a morning at EPCOT, which is very walkable from the hotel. Pack up and leave luggage with the valet. Have a change of clothes in the front pocket of the luggage. Get back to the hotel by 1ish. Uber to airport and be there by 2:30-3:00. Relax and read some until flight time.
- Choice 2 is a lazy day at the hotel. Late breakfast. Maybe a little pool time. Works perfect if we can get a late check out. If not, we pack up and leave our luggage at the valet. Head for the airport around 2. Always want to not be rushed at the airport. Especially MCO where things can bog down and get slow very quickly.
Make the flight choice that is most comfortable for YOUR plan. You're going back to the real world so do what makes that transition easiest.