For one thing the outlet was installed wrong. The way it is now water is sure to get in behind it. Once water gets in it's going to keep tripping.
Should have looked something like this.
http://www.stpaulroofing.com/Exterior-Siding-Windows/Siding-Accessories/Siding-Electrical-Block.jpg
Should have looked something like this.
http://www.stpaulroofing.com/Exterior-Siding-Windows/Siding-Accessories/Siding-Electrical-Block.jpg