The status that you are getting back for the uploads is -1, this means that the upload was not triggered. Are you testing the on the update page or the insert page? After you add in the debug code to the page you will need to load the page and attempt to upload on it. After you attempt to upload the files the debug info should give back more information if there are any problems.
It looks like you are using different triggers on the insert and update page, you should have the uploads set to the button pressed trigger for both of these. For the insert and update server behaviors you can set the trigger to 'all uploads successful'. This will make it so that the update and insert do not occur if the upload was not successful.
You should try going through this with the debug code on the page and upload the files. It should give you some info about the files and why the upload failed. Are you running into any size or timeout problems? By default the php upload and timeout values will make it difficult to upload larger files. If this is the case for you the php.ini file will need to be updated and these two values adjusted.