I've done the "fly in late and then drive 1.5 - 2.5 hours" thing too many times. Sometimes it winds up being the most convenient or cost effective, but it's still not fun.

Speaking of convenient and cost effective, I'm surprised by your dad's choice to take a connecting flight on DCA-RDU instead of driving. The door-to-door time on the connecting flight is almost certainly worse than the ~4.5 hour drive time, and he needed a car at the other end anyway. ...Speaking as someone who has done that route countless times and virtually always driven it.