When I use a 5 gallon can, I stand on the front axle on my JD to pour fuel into the tractor. When I use a can to fill my Kubota, I stand on the bush hog or whatever implement is behind the tractor. But most of the time, I just drive it down to the nearby fuel station and fill it up using their pump!
A partial can is a lot easier to handle than a full can. Consider pouring from your 5 gallon can into a smaller can, such as a 1 or 2 gallon can and then pour that into the tractor.
An electric pump is also a way to go, but they require power and are money spent that isn't required to be spent.
David from jax