Whenever I opt for 'roadtrip', almost inevitably, about 4-5 hours in, I wish I were flying. When I fly, I don't usually say "oh, I wish I'd driven" (unless there's a delay or problem).

As I've driven more, I need to allot myself more stops. If a trip is over 10 hours, I'll probably split it in 2 days, and stay overnight some place. 20 years ago, I would have 'pressed on', but... it's usually not worth it any more. But some of the 'cost savings' of driving go away when you factor in hotels.