Well, what I did was have a 300-gallon skid tank of off-road diesel set up behind the garage, refilled periodically by the same folks who provide our normal heating oil. Hand pump on it. Just stick the nozzle in and crank for a while.
When the big ice storm hit last winter, I was glad I had the extra storage, as the tractor was running 24x7 turning a generator. Of course, in that situation, I was back to filling again with 5-gallon cans.. which was kind of a hassle.. for all the reasons so well-articulated by others. One foot on the operator platform, one on the right front tire, etc.
Maybe someday I'll rig a pump to get the fuel into the garage in case of another extended power outage. Not sure it's worth it.. but during the outage I smelled of diesel the whole time. Get up in the morning, pump some fuel into the cans, lug to the tractor, fuel it, go to work, come home, do the same thing again, and on, and on, and on... power was out a bit over a week here.
This was a time I was glad I had a manual trans.. as I'm told otherwise the HST fluid would have been pumping the entire time. As it was, I just shut it down once, changed oil and filter, and brought it right back on-line. Easy maintenance, although the hour meter went up a bit. /forums/images/graemlins/grin.gif
Guess this rambling is to suggest that, if you have any plans of generating power with diesel (whether with your tractor or a standalone unit), having plenty on hand is a good thing. Without power to run the gas station pumps, I'd have been out of fuel in a day or two if just relying on my two 5-gallon cans.
Bob