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I don't think the pick up tubes go all the way to the bottom of a 55gal drum. That would not be a good thing as it would pick up any water/sediment.
In a 5gal can, it goes in at an angle to the opposite corner of the container so sealing against the bottom is not possible.
Having your external fuel source mounted/situated higher than your genset is asking for a siphoning problem. The pump should lift and transport the fuel from any source at the same level or even lower(within reason) than the genset.
I would never situate a fuel source higher than the genset...