I have a couple of 44's (gallons - ours are bigger than yours) which I fill at the local servo, then unload them off the ute (pickup) at home with the help of the bucket or forks. Then an armstrong rotary pump to fill 20 litre oil drums - I have five of those.
Come refueling time, lift one of those onto the floor of the cabin, and siphon the diesel into the tank.
Current tractor tank holds 95 litres, and I've always used a calibrated dipstick before each day's work to check whether the tank will take another 20 litres.
A previous tractor, a Fordson Super Major, with a tank mounted high up level with the steering wheel, was a real pain. Required a balancing act to perch a 20 litre drum on a plastic milk crate balancing on two timber offcuts on the fuel tank to keep it level. I was glad to see the back of that system!