We stand the drum up in the truck for the trip to the oil depot. When we get home, we gently lay it over in the truck. We raise the bucket on the FEL to the height of the tailgate and roll the drum into the bucket, strap it in with tie down straps, and head over to the raised platform. The platform is a good sized wooden deck (about 5' x 6') about 5' off the ground. We raise the bucket up to that level, roll the drum onto the platform, and block it in place with a couple of 4x4's.
I have the drum plumbed with a vent setup with a ball valve in one bung hole and the hose plumbing with a ball valve in the other bung hole. We roll it so the vent points up and the hose valve is at the bottom. I re-attach the filter and hose assembly and we're good to go.
I am going to make a couple of improvements to the plumbing. Right now, we unscrew the vent from the 2" drum hole when we get to the oil depot to fill it, and use the pipe threads to unscrew and re-screw the filter to the hose valve. I don't like making and breaking the pipe threads that often, so I'm going to install unions on both joints. That will also stop the samll amount of fuel that leaks when I turn the filter unside down as I screw it back on.
Just got my third drum full in 7 weeks; we've been using it to fill the big rental loader as well as my little TC18, and also to start burn piles until the dry weather forced a burn ban. Once we get past this clearing stage (almost done), I expect my usage will drop considerably.