Hi user "Beachball" can you check to see what size those pictures are? Here are the limits for using The picture / video messaging portal, formerly known as PIX Place:
More then likely your photos are larger then the 3MB or 6MP
The resolution settings for your camera are:
Try using a lower setting.
For the existing photos can you download them directly into your computer and upload to http://picture.vzw.com/pub/gallery.do ?
Hope this helps but if it doesn't please reply and let me know so we can go to the next step for a fix.