Sure! Do you want some coffee too?

Hi,
Did you ever get an answer to your question? You might get a better response if you were more specific about what you need help with as well as posted it in more relevant forum section (e.g., "Template Questions".)

Have you completed the tutorials at http://doc.silverstripe.org/doku.php?id=tutorials? That will get you pointed in the right direction.

If you wanted to make an editable sidebar with an image and content, you could do something like the following in your Page.php.

<?php
class Page extends SiteTree {
static $db = array(
'SidebarImageCaption' => 'Varchar(50)',
'SidebarContent' => 'HTMLText',
);

static $has_one = array(
'SidebarImage' => 'Image');

function getCMSFields() {
$fields = parent::getCMSFields();
$fields->addFieldToTab("Root.Content.Sidebar", new ImageField("SidebarImage", "Image"));
$fields->addFieldToTab("Root.Content.Sidebar", new TextField("SidebarImageCaption", "Caption"));
$fields->addFieldToTab("Root.Content.Sidebar", new HtmlEditorField("SidebarContent", "Content"));
return $fields;
}
}

class Page_Controller extends ContentController {
....

}
?>

This will create a "Sidebar" tab in the CMS admin that you can add an image and text to.
Hope this gets you started,
Sam