You would need to develop your own secondary Lopp with a custom query for this. See http://codex.wordpress.org/Function_Reference/WP_Query
I understand how to query the database, but I want to create something in the admin tool that allows the user to select from a list which posts to add in the sidebar. How can this be done?
The only thing I’ve found is the Options add on for Advanced Custom Fields which stores all this information in the options table.
http://www.advancedcustomfields.com/add-ons/options-page/
You could base your query on a specific custom field. That would allow the user to define which post are included in the final list. Which, I guess, is pretty much what that plugin offers but if you opt for a coded solution without the plugin, you could look at building your own custom meta box in the admin area.
The problem with this custom field is that it is on a per post basis and I ideally want to define all posts to have this custom field form one page in the admin tool?
Sorry – I’ve not seen anything that can do this.
