Uploading an Image is confusing to users

The current placement of the upload image button is confusing to our users. We've had multiple requests to add the ability to upload images in a status update even though the functionality already exists.

Our proposed solution is something we are not able to implement because the plug-in doesn't offer any state classes on the wrappers to be able to modify the location of various things at various steps in the process.

Attempting to implement our proposed solution results in issues like this. Can you work up a solution for us? Another possible solution would be to add a fourth button (beside images, video, and links) that allows the user to upload files.