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Is now a bad time to buy a MS75D

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Backhanded compliment, criticism or sarcasm.

Yes, I think the 100 supercharges about 15% faster in kW/h initially but the bigger issue is the tapering of the supercharge curve. If you needed 75kWh to get to your destination, I think the difference could be half an hour.
 
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Is the charging actually measurably slower?

Charging speed at home is exactly the same.

Charging speed at a Supercharger is faster per mile added with a bigger battery. Think of it this way: it takes x minutes to fill a battery to a given percentage at a Supercharger. So the bigger the battery, the more miles you've added when you reach that percentage.
 
Charging speed at home is exactly the same.

That’s not exactly correct. The 75D has a 48amp onboard Charger and the 100D has a 72amp. With the HPWC, they are the same if you are using up to a 60 amp breaker setup (48amp at the car), charging at 34mph.

But the 100D can handle up to a 100amp breaker for a charging speed of 52mph.