Have a look at my guide here – http://www.wpexplorer.com/wordpress-tinymce-tweaks/ – so you can see how to create a popup window where you can select your options than insert a shortcode. If you download my Free Symple Shortcodes plugin you can see a live implementation as well.
Instead of having the user select the posts to insert instead add a Categories taxonomy to your portfolio so the user can organize the items into categories. Then you can have a simple dropdown in the popup window for the user to select what category to pull posts from.
This is much easier for the end user to manage in the future since they just have to add their posts to the category and the shortcode will automatically display them without having to manually update the shortcode to include the new posts.
- AJ
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