Another thing to consider is that if you live in a cold weather area fuel suppliers will usually winterize their fuel. I know all the gas stations and bulk suppliers here where I live do it. Where a guy might run into trouble is if you travel from a warmer area, where they don't winterize, into a colder one. Just this past winter we had an early cold snap, down to about 20 below zero or so, and I went out to fire up the old Rabbit one morning and sure enough, she was gelled. I hadn't fueled it for quite some time and it still had summer diesel in the tank. I just let her sit for the week or so that the cold spell lasted (luckily I have other rigs I can drive), until it warmed up enough to where I could get her started and then got some winterized fuel in it, didn't have a problem the rest of the winter.
I am fortunate that I am able to get fuel out of a card lock that posts it's diesel temperatures on the pump.
In the winter I am able to choose from a couple temperature ranges.
Really, the scenario I would typically run into is where I have a tank of diesel I filled up early in the fall (summer fuel) and end up running in mid November where temperatures can be down to -14*c
Just enough to be iffy on that summer fuel....