That's what I was thinking - the prop mistress is gonna have to build this with pockets inside for those smaller items that cover the gag of the big stuff.
I have sent a note to some magician friends as well - but it's an arena style, 3/4 thrust stage so things really need to be dressed well, since the audience can see stuff from 3 sides and are only 10-12 feet away from the stage edge.
[on edit] a magician friend who knows the space suggested building a bag with a bottom layered fold held together by 3 strong magnets, the actor pushes thru easily to go into the trap, and the last item is a big one needing two hands, so the act of closing the bottom is masked.