Outlander 800 in a shortbed … with a toolbox?

I’m relatively certain that the answer is a resounding NO, but I’m trying to buy an 06 GMC 2500 Allison/Duramax crewcab shortbed with a combo tank/toolbox, which of course wouldn’t leave much room for an Outlander in the bed.

Has anyone successfully carried an Outie in such a vehicle with the rear resting on the tailgate? Bad idea, right?

Hope springs eternal.