When you’ve got problems sending pictures and are using the resize option with your content protection enabled BlackBerry you should check your media card. If you send the picture without resizing you have no problems.
Go to Options / Device / Storage and use the menu button to remove and re-insert the media card. If you get a warning telling you there is an encrypted media card you have to (re)format the card. Part of the previous content protection is still active on the card and only a format removes it.
When you try to send a picture and use the resize option I presume a temporary file is being created on the media card. Creating the temporary file fails, probably with some uncaught exception, when the media card hasn’t been reformatted. The outgoing mail will just sit in your queue with a status of “resizing 0%”.
Most common causes for this issue are a security wipe of the device and the device being re-activated or a new device password being specified.