Adding attachments to feature during editing session is essential but when you have multiple attached files you loose the controls of what they really means because the unique information stored in the geodatabase is the original filename of the uploaded image.
It will be great to have a widget that could :
-upload the file (image, doc etc)
-edit the fields defined in the attachment table (for example dat or description of the photo aploaded
Actually this seems not be possible ether in deskop application (Arcmap) either in any web application (ie WAB)