I am building an illusion were a very long sword has to go through 4 layers of the prop, getting the sword through the first and second holes is no problem as the girl inside the prop can help but then the magician is on his own to hit the other holes. Does any have any thoughts???

Once you make it through the first two holes.. the rest should be easy...

you have a built in guide wiht the first and second hole..

Right! if you have the holes aligned properly, then the first two should act as a guide for the rest of the travel.
If it seems to hang a bit, then try making the upper <leading edges> of your holes in a slight V or funneling shape -_/- so that the action is smoothed out a bit.
Good Luck
Kay