A system and computer-implemented method for facilitating a user of a mobile device obtaining image data of damage to a vehicle for damage assessment includes capturing image data of a vehicle with the mobile device. The mobile device may include an orientation model for capturing the image data. The captured image data is analyzed, and a determination is made of the orientations of the images of the captured image data. In addition, a determination is made as to whether the captured image data can be used for the damage assessment. The captured image data may then be transmitted to a damage estimator computing device for estimating an amount of damage to the vehicle.