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I’m very new to Tortoise SVN and have previously used Microsoft Visual SourceSafe. With VSS I can “Shadow” a file when I check it into source control. This means that when the updated file goes to the repository it also physically is moved to the development server in “one” button action.
Is there any way that I can reproduce this ability via a plugin or a setting change?
This is a Subversion issue rather than a TortoiseSVN issue (TortoiseSVN is the client that provides the integration with the Windows desktop, Subversion is the actual server).
But to answer your question: yes, you can do this, using hooks. You will need to do a create a post-commit hook that does the required work (probably an “svn update” command) on the development server.
Here is an example of someone doing that in a Windows environment.