what is the best way to add things to a side bar

As you seem to understand from your tags, the user (who would need to have admin-level privileges) can add things to a sidebar via Widgets in Appearance > Widgets. For text and images, the default would be to drag the Text widget into the sidebar, then edit to add the text/image reference.

To make this super-easy for your user (assuming they don’t have any knowledge of HTML) you could install the plugin Page in Widget. This plugin lets you display the contents of a WordPress “Page” in the sidebar. The user would create a Page, upload images and format their text, then “Publish”. Going over to Appearance > Widgets, they’d then drag in the “Page in Widget” widget into the sidebar, choose the correct page from the dropdown, and Save.

If you’re looking for a really high-level look at how to administer stuff in WordPress (for either yourself or your users) I recommend http://learn.wordpress.com/ – best of luck!

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