We are implementing SharePoint 2010, and want users to be able to drag and drop documents into a library and having the Content Type applied dynamically.
What is the best way, in your opinion, to do this?
you can add an event listener or workflow to the generic list item in the library and bind it to the item added event then parse the file name extension to determine the content type.
The Content Organizer tries to solve a similar problem.
This blog describes some of the techniques it uses.