To the administrator:

You may want to consider adding the below mentioned add-on. This allows for a small popup window to open and the user may select images from their gallery. "When creating or editing a post, your users can open a popup window that will show them their pictures in the chosen gallery, albums or attachment system." It'd make things a little more user friendly for those that are not as computer savvy.

Here is a shot of what the popup would look like to select from the gallery:


Add-on: http://www.vbulletin.org/forum/showthread.php?t=243865