On a disney vacation, we'd usually leave mid-morning both ways, since it is a 2 hour drive to/from the airport.
We're west coasters, so DW and I try to fly out in the evening on a red-eye that gets us into MCO at around 6am. This gets us an extra day at WDW.
Not everyone can handle doing this because if you can't get any sleep on the plane, you'll likely crash by mid-afternoon. It works for us though, and we've done it several times.
We always fly non-stop to MCO and it is only a 2 and a half hour flight, so no need for a red-eye.![]()