My move into digital humanities work has taken the usual route. I began a traditional teaching project–having students write about landscape, urban history, and place. Gradually, I moved toward having students make their work available to the community. After public presentations and radio broadcasts, I began to explore having students create web materials, which led to the cultural gardens site. That process began with me doing the design on a server, using static pages. Gradually, we began to work with a local web design firm, and then I found blogging. And, more recently, we have begun to integrate tools, especially thinking about Omeka from the Center for History and New Media. But, even as we have expanded tools and rethought how we use them in the classroom and for public outreach, we have not addressed what I see as a more fundamental strategy. Namely, how do we create a package of sites and materials, without each time reinventing our projects and having to do back end maintenance on technical infrastructure? Or, perhaps, this is the nature of the beast? Would a strategy at the infrastructure level, have led us to better solutions, earlier in the process? Is it possible to begin with technology and work to a project or is it preferable to work from project to technology?