The only time I add fuel treatment is in the fall when it gets near freezing, as the retailers all sell treated diesel in the winter months so just need to treat what summer fuel is in the tank. Usually try to run the tank down to a few gallons before treating it as it takes care of any moisture in the filter. I regularly drain the tank sump to check for water and have never had a fuel issue down to -25.
I've been running the tractor in winter (not a whole lot) since I got it without any problems. I added 5 gallons in December to an almost empty tank and another 4 gallons this last Thursday. This all started immediately after I added that last 4 gallons. Can't say for sure but I think I might have gotten some water with that last 4 gallons. The slush that came out of the filter bowl seemed to me watery.