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The Complete Idiot's Guide® To WordPress by Susan Gunelius

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WordPress.org Similarities to Word Press.com

As discussed earlier in this book, it’s always a good idea to start a free blog with WordPress.com so you can play around, experiment, and get to know the features of WordPress before you dive into using WordPress.org. This makes the process of self-hosting a blog with WordPress.org far less overwhelming.
 
WordPress.org and WordPress.com are the same application. However, because WordPress.com is hosted by WordPress, Automattic (the company that owns WordPress) includes features through the WordPress dashboard that enable users to readily access other Automattic-owned tools, test new tools, and create a sense of community among WordPress.com users.
 
On the other hand, WordPress.org enables users ...

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