Use the space between the handle rods to carry a small umbrella.

Have the handle have a pop out extensions on either side so you can hang a jacket on it

I too would like to see someone figure out how to get a full size spinner (22x9x14)

Put the wheels on the personal item and then make a hardside bag that is max size (22x14x9) that mates to the top of the rolling personal item and can be detached.