I recommend re-exporting your SSL certificate as a PFX file (including private key) with a new strong password, then updating your bindings with these details. I'm wondering if your browser might be inserting a saved password before you hit the save button at the end. Beyond that it is possible the certificate file itself is corrupt, so the export and update should help here too.
As to the error about duplicate bindings, this is something that can be displayed when you are updating an already active port. To be safe though, do a quick check of the bindings to make sure you don't have any duplicate bindings on the port/IP, then when finished updating your bindings please schedule a restart as this should flush out old binding information. Hope that helps!
Kyle Kerst
IT Coordinator
SmarterTools Inc.
www.smartertools.com