It seems like the charge right before he stalled was the issue. I know he wasn't at a super charging station but he probably should have spent a couple of hours re-charging it instead of an hour. Cold weather and running something that is power intensive (the heater) will drastically effect your mileage if you are relying on a battery to power your car. Tesla probably should do a better job of communicating this but…
If the battery meter can't cope with typical American temperature ranges yet it being sold in these areas, yeah, it's a flaw. If it says 100 miles left and after 10 miles now tells you 50, yeah, it's a flaw. Can the flaw be corrected? Maybe, maybe not. But it's still a flaw.
I bet he probably could have gauged it by jumping in the car turning it on and then starting the heater as well. His mileage would have declined before he even started driving.
Think of it this way, batteries always improve in 2nd / 3rd gen devices (look at apple) and I am sure that is what Tesla will start to address.