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Will I make it?

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I disagree completely, Andy! Did you notice how he proceeded? He did everything just as he was told by those in the know. He watched his gauges and drove accordingly. I would assume he would have done the same on a colder day and perhaps even adjusted his temps too. His increase in confidence is well deserved.

I agree with Andy as well. People suggested starting it off slow. Driving at 75mph to start uses a lot more energy than 65. He was paying close attention though and did all the right things.
 
Unless I missed something he didn't have a backup plan for charging between the supercharger and his destination, or for gaining any real charge around his destination, before heading back to the supercharger. If it had been significantly colder I think the OP would have encountered some real difficulty that he hopefully would have recognized before heading home. If it had been somewhat colder, and then had started to snow while he was headed back to the supercharger, he could have been in real trouble.

There are many L2 chargers in the Milwaukee area for emergency charge on the way back and there are no L2 chargers at his destination for top off. Thoughtful planning is important in a trip like this but paralysis is not. If it were snowing, or snow was likely, then you simply don't make the drive. Same thing for significant headwinds. Under the existing conditions he did the right things. And driving fast, seeing a faster than desired reduction in buffer, then reducing speed is an ideal behavior. I really don't see much room to criticize either results or decisions here.