I use the gas can with the boat sitting in a hoist, just like always. Why ? Why not. The one and only lake pump is ~4 miles away one way. A nice ride for sure, but easy to dump in 5 or 10 gals and not spill any. I will figure out if vent is plugged somehow.
As for the pouring of gas from a plastic or metal can, I've spent a lifetime of pouring gas from cans into gas engines. Really.
"As far as the sleds, why gas cans? You have to fill the cans at the pump at the same price as if the sleds are filled themselves?"
Its not always the dutch factor. I find it much easier to have 20 -25 gals gas in the garage.
In fact warm or cold its convenient.