Unless you get a bad batch of fuel and notice your filters filling quickly I wouldn’t bother. My family has never done this in 35+ years of owning a half dozen tractors. In that time we have never needed to even drain the water separator on any of the tractors. Fuel filters have been replaced during oil changes just to be safe. We have always either fill up directly from the pump or from cans stored indoors.
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2017 2038r 72” MMM Command Cut 220r loader
The phrase " drain water from fuel tank and replace fuel filter " exists in literally every tractor owner's manual. Since there isn't a water drain valve on the fuel tank, everyone interprets the first part of the sentence to mean "drain water from water separator".
As for changing the fuel filter annually, I don't mow with my tractor and only put about 25 hours a year on it. I only use on-road diesel. As such, I change the spin-on fuel filter every 2 years.