I have a sillouette of my three boys when they were really young, 12, 10. and 6 and I love it. They did a silouette of each of the boys then layered them from biggest to smallest.
I am taking my three boys to FL again in May. Although they are now 27, 25 and 21, I want to get another silouette of the three of them.
I saw the "cutter" last at a small cart near the Hall of Presidents in MK. I am sure he/she is still in that area of MK.
I am not sure if they can cut multiples but they cut so fast that it wouldn't take them long to make another. I don't remember how much they charge, but it is WDW so bring lots of cash. Peggie