Getting the tail up to level position can be pretty tough with something like a skywagon.
Besides being heavy, just grabbing onto the tailcone is kinda like trying to catch a greased pig.
I use a long 4x4 across the t/w assembly just ahead of the tire, with a guy picking up on each end.
Alone, a duct jack as shown or an engine hoist would come in handy to get it up close to being level.
(FWIW I once weighed an airplane by myself, with the mains on scales and the tail with a fish scale hanging from an engine hoist)
Once it's up on a table or something, it isn't too hard to get your back under it (after degreasing of course!)
and raising it enough to slide more cribbing or a scale under the tire.
Remember to be careful, you don't want to let the tailwheel roll off that 3 or 4 foot high table and crash to the ground...
and probably damage the rudder on the way down.
I like to chock the mains on the scales until it's time to actually write down the weights.
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