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The covers are fairly cheap, and fold up small, so you might as well own one. However, if you're having to wonder if/when you should put it on, then you probably don't need it. It becomes fairly obvious when you do, because the truck idling for an hour won't budge the temp gauge needle off the 165°F base marking, and it will take 20 minutes of driving to do so. I totally understand that some of the fun of these trucks is obsessing about all the details though... so I get it.It would be nice if there was a small Velcro flap that you could reach for us southern people that get weekly temperature swings all season. It was 72 last week and 34 today.
It's 8°F right now for me, and that's the kind of temperatures where it starts to make a noticeable and welcome difference (<25°F?). I ran the first couple winters without one and was ok, but on days like today, I would drive 25 miles before it would warm up. If I were only to decide based on "need", I would probably only run the cover from December-February. Instead, I put it on and take it off when it's actually warmer (November-March), simply because it's less of a hassle to do when it's warm out, than when it's actually cold enough to need it.
Here in Colorado, we get roughly 40-50°F swings between day and night, so even mid-summer it will be below freezing in the morning when up in the mountains camping. The truck is fine, and aside from extra cranking to get it to start, it doesn't even cross my mind that I need to put it on then.
Hopefully that information helps.