Custom User Field Rotation


Ok so this is what im trying to accomplish... I basically created a custom user field for a certain group, that group is able to add to that custom user field and then the custom user field shows up in the designated spot.. Almost like an AD system where the user/member can add to it by utilizing the custom field.
What I'm trying to accomplish is to have the field rotate.. instead of having like 5 members add to it and then there are 5 images in that location is it possible to program it so that it randomly rotates through the images added by the 5 members? I know there are ways to do rotating ads but im trying to simplify this so that I dont have to add them to the back end but the users in that group can add it by using the custom field.