Starting in 2002, The Site of Big Shoulders began to participate in local arts events, including the Pilsen Artists Open House and Around the Coyote art festival. For these events, The Site of Big Shoulders would sponsor the exhibition of artists and photographers, and concurrently publish online articles showcasing the artists' work. These events also often included live music, particularly for the evening receptions.

Although The Site of Big Shoulders existed as a formal not-for-profit entity, it had always lacked an actual office: Meetings were typically held at staff members' homes, and a virtual office environment enabled remote work. That changed in 2007 when Salvage One, a Chicago-based architectural salvage and furniture store, offered The Site of Big Shoulders a space in its warehouse to use as an office. The Site of Big Shoulders used the donated space between August 2007 and May 2008, and then moved to its current office at 1543 North Milwaukee in the Wicker Park neighborhood of Chicago.

During this era, The Site of Big Shoulders also invested heavily in deploying Web site technology to assist managing the content of the Web site.  The Joomla content management system (or "CMS") provided a platform for publishing site content, and new features were produced and presented within Joomla (while links to static vintage features were retained and integrated into the system).

The latest iteration of this platform is SOBS 5.0, deployed in February 2012.  This includes an upgrade to the latest version of the Joomla content management system and related software, full migration of all vintage content into the CMS, deployment of a new design and layout for the index pages of the Web site, and an overhaul of the site's Joomla template frameworks to support fast and easy deployment of content into custom designs.

Since 2010, The Site of Big Shoulders has been producing Art+Poetry Chicago, an annual program that brings together the poetry and art of the Chicago area.  This includes a poetry contest, an art contest based on winning poetry submissions, and a poetry reading and gala reception that brings the art and poetry together.