Comes down to where I’m staying the night. Navigate to the checkpoints rather than the final stop. Easier, manageable pieces.

I'd ship the car and fly.

I took a ‘17 civic from Ft Lauderdale to Seattle. If I were you, especially as winter approaches, I’d consider a more southerly route that takes me through Moab, UT and the desert states. Very pretty and honestly a nice recharge after looking at nothing for hours! Good luck!