If you live rural stored gas and diesel is a way of life. The nearest station is 36 miles away. I keep 300 gal of gas and 800g of diesel around. The cheapest time to buy gas is now or in the spring. The cheapest time to buy diesel is Aug/Sept. This is due to fuel blends and market supply and demand. I go thru 300 gal of gas in 6 months so I usually don't add a preservative. In you scenario I would, even in the absence of ethanol. In a perfect world it would be stored in a temp controlled environment. W/O that please keep it out of sunlight. Sunlight will heat it enough to cause it to expand and cause your tank seem to split!! I have filled my vented 300 gal tank in the evening, only to find the next day at 2PM gas flowing out the vent because it had expanded and exceeded the tanks volume. I put some in 5 gal tanks immediately, but still had the smell of gas for several days (nobody smokes on my property).
Diesel will store a little better but in the fall and spring when night to day temps can swing 40*, it will collect water. Water separation filters help but the best thing to do is pull your fuel 1-2" off the bottom and not try to get the last drop.
Good luck finding a hand pump that doesn't drip. An outfit in KS (GPI - I think) makes the best. If you empty and refill a lot (3-5 times a year) the stress from using a hand pump will cause hairline cracks and metal fatigue in the top of your drum. You won't notice this until your drum is in the rain/snow and water gets into your fuel - yes, I speak from experience!!
I usually fill 5 drums at a time (anymore and the steering on my p/u gets squirrelly), bring it home and transfer it to my bulk tank via Harbor Freight's air operated pump. The pump works great and is only $40 or so. It does require a compressor that can be regulated down to about 10psi. The electric pumps work but are around $120-$220, so I went the air route. Takes about 8-10 min to empty 55 gal.