Great breakdown! I'd like to add train to the options. OP might be able to utilize an Amtrak train for a portion of the trip depending on the travel destination. Here's a map of their routes. Tickets can be purchased online, they offer assistance for disabilities, and they have places to lie down or eat food.
If you decide to fly OP, consider getting a pack of gum to chew on to help with pressure/popping in your ears during altitude changes of takeoff and landing.
Changing hair styles specifically for the car reminds me of some emergency responders who were talking about the horrific crash scenes where people wearing plastic hair claw clips that broke apart and become shrapnel or the clip simply lodging in the skull through blunt force contact (usually) with the headrest.