Beyond a 5 hour drive, I like flying. It saves time and I don't have to deal with morons on the road. It's less stress IMO. Just show up at the airport on time, fly to destination, pick up rental car, and go. I've flown a ton for work though, so being at the airport just feels like routine.
5 hours makes sense as a break even point- as long as the airport is super nearby your destination... i can likely drive it just as fast if not faster than the airport situation will likely take.
for instance- 5 hour drive is st louis from my house
From my house to ohare is about an hour, let's leave 20 minutes on top of that if i have to park in an economy lot- since if you fly out of there frequently- you know the tram is likely down and you gotta find a buss from f or e lot then ride in the loser cruiser all the way to the terminal....
get there an hour before my flight (not two hours, I'm pre like you likely are) but i want to have a beer... so now we are at 2.5 hours almost from the time i left my house... quick google, flight time is hour 15... so now we are at 3:45, and you haven't gotten off the plane, wandered the shit, or driven the 20-30 minutes from the airport to my final destination.
throw in any delay at all and i likely could have driven there quicker.
the pickle i have where my wife is from- is there isn't an airport for 2.5 hours or so in any direction.
so do the ohare dance, fly the hour 15, then stilll have another 2 and a half hour drive at minimum, shoulda just flown to begin.