By default when you upload multiple files they are stored as the default 'Document' Content Type. Since I had a lot of templates to upload (over and over again) I created this tool to ease the pain.
It's a Windows application that can upload multiple files directly as a specified Content Type (with filled in metadata) by passing a property bag containing the Content Type and metadata values.
This application was designed to work with WSS 3.0 (or MOSS 2007) and requires to be run locally on the SharePoint Server.
Visual Studio 2005 Project + compiled application
Remote connect to the SharePoint Server and run the application. The left pane allows you to navigate to and select the files you want to upload. The right pane connects to a SharePoint Library and retrieves available content types with metadata.
Select a Content Type, specify the values for the metadata and start uploading the checked files. You can leave the metadata values empty to exclude the metadata item from the property bag.
A good tip for Microsoft Office Documents:
You can set up your document's properties using the internal field names of a Document Library to automatically fill in the values. This is called Document Property Promotion.