With every fill/empty cycle of a jerry can, you run the risk of dirt/moisture contamination. A little bit here, a speck there, and before you know it, plugged up filters (or worse) A properly filtered storage tank with "gas station" type nozzle is not only EXTREMELY convenient, you'll keep your fuel in better condition.
When I was farming, I had a 375 gallon tank. Our local Co-Op serviced the account. At certain times of the year that was barely a months supply. During the winter, use was less, but I burned diesel (in conjunction with wood) to heat my shop. It never had the opportunity to get "stale".
Then I quit farming and moved to a much smaller place. Fuel consumption was cut down to 20 or 30 gallons a month in the busy season at first. Fortunately, there's a gas station just minutes up the road with an off-road diesel pump out back. It was oh, so simple to just drive up the road and fill there.
Then I had an attack of ambition. I started up a bush hogging business with my son and son-in-law. We're burning as much as 250 gallons a week on regular basis. Because of the mobile nature of the business, we've set up one truck as a service vehicle. It has an air compressor, generator/welder, tools, tire repair equipment, and a 200 gallon transfer tank that is filled as needed at that same gas station.
I'd just as soon take a beating as fool with 5-gallon cans.