While it's better if the tank is full, I wouldn't go to any great lengths to fill it up. I usually have about a half tank and never had any issues unless the vehicle sits enough to have summer fuel in it still. If you're in a colder area, they switch to winter blend pretty early in the fall. I have 3 diesel vehicles that we use year round down to about -10F in the really cold days, and I quit using additive years ago. The best thing you can do is make sure you drive it enough to have fairly fresh fuel in it.
By the way, fuel gelling is only an issue with the engine running, unless you have a generator or something using diesel. Otherwise it'll just melt the wax when the weather warms up again.
Condensation should be taken out at the water trap on the fuel filter if you drain it once in a while.
Buying fuel at heavily used places is good advice.
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