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Currently I have a custom post type and I would like to have some different version of it based on user input - so for example when creating a post the user can select if the post is Featured or Free and then there would be an if-else statement that would display different image if Featured and different if Free in the actual post. Can anyone point me to the right direction? Any advice greatly appreciated.

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This sounds quite a bit like the Advanced Custom Fields flexible content field. Basically it works by letting you setup a number of different templates for how you might want to create/display your page. Then when you are in the editor, you pick which template you want to use. More info here: http://www.advancedcustomfields.com/resources/field-types/flexible-content/

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You can use Custom Fields or Custom Taxonomies to do this.

The easiest way is using Advanced Custom Fields plugin.

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