I can't wait until my family arrives at the twenty(ish) point of our trip countdown Tracy; we're still hovering around 90 days!
As for those silhouettes, they can be done in the Magic Kingdom. We visited a kiosk area just across from Sleepy Hollow (which, by the way, has the most scrumptious ice cream cookie sandwiches ever) in Liberty Square. My Moms Panel friend, Erin, visited a kiosk on Main Street when she had silhouettes of her three daughters made. You can read about her experience
here.
Thanks to Erin, I now know you can also find silhouette artists at Downtown Disney and near the France pavilion at Epcot's World Showcase.
Just one more piece of advice to pass along: depending on the ages of your child(ren), you may want to plan to visit at a location that is somewhat secluded during an off time. The kiosk in Liberty Square, for instance, was very quiet near closing time when we went. Because your child(ren) will be required to sit fairly still, it may be easier to get cooperation in that respect if there isn't a whole lot of distraction. I'd avoid parade time, for instance. Of course, if you have older children it isn't as much of an issue.