Flexible web page template building systems, methods and applications using an auto-expanding user-editable content container(s) are presented. A web page template displayable on a user display is configured with at least one auto-expanding user-editable content container that includes a predefined top portion, a pre-defined bottom portion, and a repeatable middle portion, The auto-expanding user-editable content container is configured to monitor the size of user-provided content in the content container relative to the size of the content container upon entry or removal of content and automatically adjust the size of the content container to fit the user-provided content by dynamically inserting or removing instance(s) of the middle portion of the content container to vertically expand or contract the size of the content container to fit the user-provided content.