My preference is:
1. Restaurant puts oil back in cubies. Load in back of truck. No pumping, quick & easy.
2. Hand-crank harbor freight pump from barrel at restaurant to empty cubies.
I tried pumping into a barrel in the back of the truck once,but all that meant was I had to pump it three times to get it where I needed it.
Unless you've got to pump any hundreds of gallons of oil each week, you really can't beat the ease of the hand-crank pumps.