Hi Bart Welch,
The easiest way will be using RadGrid bound to the list of ContentItems. If you want to use a table there are two ways.
1. Create a custom class that inherits from ContentView. In this class Find the basic repeater and set it as not required. Then modify the template for your custom control. Add a new repeater control. Inside the ItemTemplate of the newly added repeater you should have three ( or more ccontrols depending on what you want to display) controls. To get the <td> and <tr> elements dynamically created you should check whether the content items are divisible by the current rows and columns. By doing so when you add a new item from the backend it will be automatically added to your table.
2. Create a static tables - say 4 by 9. This means 36 cellls. Create a custom control with WebEditor that could select shared content. Generate 36 simple properties for your custom contriol. For each property you should add or remove a content item using the WebEditor. This will allow you to remove or show a certain items, but this should be manually done.
I hope this helps.
the Telerik team