Variety is the spice of life!!! I am from MA and we have flown, driven, and may take the auto train next year, just for the experience!!! If we have a short trip planned - less than 7 days - we fly. Next summer we will be gone for 3 1/2 weeks - so we will drive to VA and take the auto train down to FL. We will visit Vero Beach for a week, WDW for a week and Hilton Head SC for a week, than meander our way north back to MA. I also want to stop at T.I.G.E.R.S. Preservation Station in Myrtle Beach. We recently saw a 900 pound Ligor at King Richards Fair in MA and would love to see more. Plus we would like to stop and visit with some cousins in Washington, DC and NYC. So, if we flew all the time - we would miss out on a lot of interesting people and attractions on the way!!! We always do something new.
When we drive we leave Boston between 2 am and 4 am. Our first stop is in NJ for gas. When we fly we leave on the cheapest flight - normally 6 am. When we drive home - doesn't really matter what time we leave WDW. When we fly - we will leave in the afternoon - so it's not so late for someone to pick us up at Logan.