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I noticed how this might be an issue, particularly on the "Tesla ends range anxiety" sound bite from March. On a trip the other day with the last stop a ways out and a return trip back to the "supercharger highway" the next leg, it was not an easy way to trick the nav into contemplating a return back the the same supercharger at which I was currently charging. Multi-destination might have been able fix the calculation.
I think it would help with range anxiety as a person can plan their day route and know how many times possibility they need to stop to charge. Similar to evtrip.