Currently, I do all of my skinning and css changes on the sites respective server. Copy and paste where appropriate to production on an as needed basis. I doubt this is the most optimal way of deploying such items. Is there a tool or resource I could use like TFS where it keeps a repository of my files, version history and version control such that when I'm prepared to deploy to production or a test site I can simply publish that server?

I haven't looked at web matrix, but is that something I could use to accomplish this? Is this concept even possible? Just thoughts to full proof development and minimize disasters as the one I just encountered.

Thanks for any and all suggestions.

Have a look at Unfuddle, https://unfuddle.com/, for the repository and Tortoise SVN .
Together they have good facilities for teams or individuals with good version control.
Haven't used it with DNN yet but have with .Net projects

The biggest problem here is that a substantial portion of your website is contained in the database. I don't know a good way to do version control on the database.

Not only that, but it's difficult to even define a "version." What would you do if you changed a setting to a module, for instance.

I supposed you're right. I don't believe there is a good to way keep versions and what not. May have to nail down a solid procedure and adhere to it.