Add span to the first letter of post

This drop caps plugin does what you are looking for: http://wordpress.org/extend/plugins/drop-caps/

If you’re trying to do drop caps this should be enough. If you want to do more you could look into the code and see how the plugin wraps the 1st char in a span. It probably uses preg replace too. Id look myself but I’m answering this on my phone and have no way of looking at the code.

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