It's not that bad. I take weekend trips between NYC and [1 hour west of Chicago] multiple times a year. At around 870 miles, it's about a 13-14 hour drive with pit-stops. I usually split the trip into 2 days from NYC to Illinois, but only because I typically leave right after work, and I certainly wouldn't want to drive overnight.
The trip back is usually done in one day, ~10am to ~midnight. This usually includes 2-3 stops for gas and food. I wouldn't mind these stops being half an hour instead of their usual ~15 minutes, but it would mean that I would have to leave an hour earlier, or get home an hour later. since I'd have 50-100 miles less range per "fill-up" with the top-of-the-line Model S, I'd probably have to make an extra stop as well.
Ultimately, I look forward to none of this discussion mattering in 10 years, at which time I fully expect 400+ mile range in self-driving EV cars that charge in 10 minutes.