What happened here has been misstated a bit.
The pile-up at the superchargers involved a lot of Uber drivers who had been using them -- not necessarily apartment dwellers. And a lot of those folks weren't especially familiar with the cars.
Cold does three things to batteries: 1) it dramatically reduces the rate at which they can be charged, 2) it reduces the voltage they will supply at any given state of charge, 3) it creates increased demand for their energy to heat things up.
As the experience of a ton of Canadians and Norwegians shows, Teslas and other EV's are fine in the cold. They can use the stored energy in their battery to warm said battery up, then go on about their merry way doing whatever they would do. If they're plugged in to a slower charger, they can even pre-warm the battery in preparation for departure. When it's moderately cold the waste heat from the motor/inverter/battery is enough to keep the battery warm; when it's extremely cold the battery needs to supply some extra power to do this.
The problem here was the charging side. These batteries charge slowly in the cold and need to be preheated or "preconditioned" -- it prefers to be at 50 Celsius for fastest charging. I believe on Teslas you do this by putting a Supercharger address into the car's sat-nav, and it will figure this out and time the preheating so it's ready to charge when you get there.
The trouble is that people showed up at the Supercharger not knowing to do this. So they plug in, their battery's at -20C, and it is charging VERY slowly until it gets heated up.
Meanwhile there's a line of people waiting in the cold. Some of them probably properly preconditioned their batteries -- which is the right thing to do if you're about to connect to the Supercharger. But they get there and all the plugs are taken up by people charging at 5 kW with frozen batteries. Theirs are nice and toasty, but they are waiting in line to get there ... while continuing to expend energy keeping their batteries at temperature. At some point they have to either turn off preconditioning or run out of energy, leading to a cascade failure.
This could have been solved with either better education about preconditioning or access to more plentiful slower ("Level 2") chargers. I don't know how those are in Chicago, but there are a zillion where I live in Syracuse.