We've met Cindy several times just by having dinner at the castle. She and the Fairy Godmother both appear in the waiting area at regular intervals for photos, autographs, story reading and other activities. The PS for dinner is much easier to get, and the castle serves the best prime rib at the MK!
Toontown Fair is a great place to see her. You go to the County Fair tent and there are 3 lines that have signs above them telling you who is in each room. Then they allow only about 8-10 people to go into each room at a time. It was nice to have your own sort of private time with the characters. You could talk to them and have pictures taken and autographs signed. We never felt rushed and the lines were not that long.
Toontown is almost a guarenteed spot to see Cindy. I've seen her several times in there... and now I've heard that there is a room that is for all the princess characters, so you may get Cindy, Snow White and Princess Aurora all together!!!
Has anyone ever gotten a picture with several princesses together?
We were fortunate enought to get Belle and Aurora together last year in Toontown during MVMCP. But we had the place almost to ourselves. Don't know if it's crowded if they would do a group picture like we got. We also got Cinderella and the Fairy Godmother together.