If you go the 55 gallon drum, they make a caddy for them that fastens on to the rim of the steel barrels and allow one man to tilt it on its side and then upright it if needed. They have 2 wheels on the edge so you can upright it, roll it to wherever you want and then lay it on its side. THE 1" and larger 2" bung accepts standard pipe threads so you can insert a pipe nipple and a threaded valve in one of the bungs and use the other to vent. McMaster Carr would carry them, but you would still need to build a stand for it to set higher than your tractor so that might not be practical.
Simpliest is just the get a drum of the size that you want, fill it at a station and use a hand pump that fits in the 2" bung. For a few $$$ more you can get a 12 volt fuel pump and power it off your tractor battery.
My fuel station is a 105 gallon rectangular tank that I mounted swivel rollers on and a 12v 15 gpm Filrite pump. I power it with a standard sized battery (650 CCA) that I keep charged with a battery minder. The pump has a 15 micron filter installed on it, then a 25 foot hose with auto-shut off nozzle just like the service stations so I never spill any fuel. I have $350 invested in the tank, hose set up from a Craigslist post and $68 for the battery to power it +$10 for the battery charger. IT is worth the $78 for me not to have to raise the hood of the tractor each time I fill. I drilled and tapped the post to permanently attach the pigtail leads for the charger but still use the alligator clips to hook up the pump. I can roll the tank easily even when full if needed. I used to keep it in back of my shop and then roll it to front for filling but now I have an addition on my shop for my boat, lawnmowers and fueling station right by the door so I just pull up, raise the garage door, fuel and go.
Bulk fuel is delivered straight to my tank from my local distributor. I have to have 150 gallons minimum but he is happy to split the delivery with me and my brother in law. I could just make it to the total by myself if both tractors were empty and my lawnmower and I used a couple of plastic containers.