I too have noticed lately that 5 gallons of anything seems to weigh more now! Same with the 80 pound bags of concrete dry mix.
This same topic often comes up when refueling small airplanes in the field. I pump it electrically, the container stays on the ground, and I let a high flow fuel pump (made for high horse power hot rods etc., around $100.00, Summit Racing) do the work. The electrical draw off my small plane's battery is not enough to matter, and the best thing is I never overfill and spill a drop. That is so easy to do when using a 5 gallon jug, up pumping electrically frees you up to monitor the rising level. Time wise, it takes me a few minutes longer (about 1 gallon a minute) but I do something else, check the oil, etc., so no matter.
If my L3301's burn rate was high enough to warrant it (it's not even close) I'd do the same as I've done in my plane: permanently mount and hard wire a fuel transfer pump, with a dash mounted switch. A screened dipstick for the inlet, with enough hose to reach, and a PVC pipe holder for it when done.
Right now, for my modest tractor fuel needs, I just dump in 3 or 4 gallons when the gauge shows maybe 3/4 empty, so no fear of over filling, and easy peasy to lift. Just a big farm funnel, I have never had any issues with water etc. and don't mess with a Mr. Funnel etc.