Good description of the switching out hands - I've noticed the same on long trips in the last year. Prior to last year, for a couple of decades, no road trips to speak of since flying was quicker and "better". However the Model S has brought back road trips - a side benefit I didn't realize when we made the decision to buy the car. But I'll be sticking with old, slow, blind, 2-wheeled (non-D) Sparky so no lane-keeping for me. Have to just do more pushups or something.
Yeah maybe pushups will do it. lol.
For me, it used to be anything under about 800-1000 miles away I don't really prefer to fly. The airport is an hour drive. Need to arrive 90-ish minutes early for security after finding parking because you never know how long that line is going to be. (My closest airport has very little expediting even if you spring for first class.) Then the flight, then deboarding, waiting for your bags, getting a rental, and then driving from the airport to the destination.
For example, my routine NC<->NJ trip (just under 600 milles driving) the door to door time when flying is 5 to 6 hours. In an ICE I can do it in under 8 hours, and in the Model S it takes about 9 on a good day, 10 if I'm not in a rush and hang out shopping at one of the superchargers longer than intended/needed. By spending a few extra hours on the road I don't have to deal with the airport, flight schedules, TSA, plane ticket costs, rental car costs, etc. Well worth it to me.
At about 1000 miles it starts looking more like flying is a better option depending on free time available. 1000 mile drive is maybe 15-16 hours of driving, plus about 4-5 hours of charging. I can still do that in a day by myself, but flying isn't much more time than the 600 mile trip... maybe 1 more hour to come to 6-7 hours door to door time when flying. ~12 to 14 hour difference each way, so looking at a full extra day of travel when driving vs flying.
I'm definitely lowering the bar for mileage where flying is a preferred option lately. I was figuring autopilot would help me keep it where it is, but not looking that way.