An intra-oral imaging system includes a handheld intra-oral camera in wireless communication with a remote computing device. The computing device includes a display unit and is linked to databases containing historical data for the teeth of a subject. A dentist actuates a touch-sensitive button to prompt capture of images of the subjects teeth, which are wirelessly transmitted to the computing device and graphically displayed. The images generally represent an arrangement and conditions for the teeth. Program modules are executable to identify a current condition of one or more teeth, and to select a prerecorded visual demonstration of a dental procedure from a database based on the identified current condition. Alternatively, the program modules may extrapolate using the current and historical data to predict a future condition and recommend procedures or otherwise alert the subject to potential future procedures. Visual demonstration of the procedures is provided on the display unit.