You can/should check your tankage with a dipstick and water-finder paste (water-gauging paste):
Water finder paste & dipstick for use in oil tanks: using a water finder paste on the end of a stick. Water indicating paste also called water finding paste or water finder paste, is coated over the bottom few inches of an oil tank probing stick or onto a string or flexible tape which can be inserted into an oil tank. The water indicating paste changes color (typically white to red, green to red,or pink to white) to indicate the depth of water in the oil tank.
You can google "water finding paste".
Consider installing water block filters instead of/in addition to your (glass bowl) separator ...and, if you have electric pump(s) on your bulk tank(s), try running the fuel through the water-block filter and back into the tank (polishing the fuel).
If you find water in the bottom of your storage tanks, you might shorten the pickup tubes of the pumps ...until you get rid of the water (by, say, purging the tanks with the pickup running to the very bottom (lowest point). [If the tanks have provision for gravity feeding (like home heating oil tanks) you can set up a drain that way.] The water-finder-paste dipstick process will show you how deep the water is in the bottom and (thus) how much you should elevate the pickup tube.
If your problem is not water, but you suspect gelling from summer-blend fuel, try a dose of Power Service 911 in the tank of the implement and see if there is improvement. Ultimately, if gelling is the issue, you can install a heated filter on the implement (Racor, e.g.) and that should keep the implement happy no matter the ambient temperature.
Let me know if any of this is helpful.