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Should I charge to 100% (night before trip) if my first supercharger stop is only 80 miles away?

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Not to put a damper on your quest, but you might check your local laws... I think that, at least at one time here in California, driving in neutral was actually illegal. No clue why, other than the reduced control you have over the car when going downhill. Not sure how anyone would know otherwise, but the car probably records such events if it came to data mining after an incident.

I've found that EVs follow the laws of physics remarkably well. What you use going up hill is pretty much returned when going down, so let the car use its regen and call it close enough.

In many states (including California and Maine) it's illegal to coast in neutral on a downgrade.