Issue 1 is normal for the basic Outlook-Addin project. For it to reference the dll in the location field you will need to create a raw addin.
You will need to remove the VSTO layer from the project then you will need to expose and register your own _IDTExtensbility2 interface implementation. Here is a start to give you an idea of what route you need to take: http://msdn.microsoft.com/en-us/library/extensibility.idtextensibility2(v=vs.90).aspx
Issue 2 I believe you are correct it does have something to do with the signed certificate. When you buy or create a valid Certificate it will include your Publisher inside it, it should then display in the options window.
I hope I have helped a little and set your on the right track :)