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#70
Hello dwsiddall, :)
Since the file you pinned to the taskbar doesn't have a file type or association assigned to it, this would be why you're having to select what to open it with.
You could create a Hosts file shortcut using the method in the tutorial below, and pin this shortcut to the taskbar instead. It will open the hosts file in notepad when used.
HOSTS File - Create a Shortcut - Windows 7 Help Forums