The tiny wheels on most any surface other than smooth and flat would be nightmare, even on small pots.
I would think that any type of bag that is not rigid on container of that size would eventually slump and you would end up with a leaning tree.
I have this dilemma with a banana I'd like to upgrade to a bigger pot. My standard dolly will work, just not very well, you need a dolly with a wide foot in order to get the levelage to tip it up. A 55-gallon would be even tougher. Mine converts to a hand cart, but you still gotta lift the darn thing on it.
I'm open for solutions.