This paper will attempt to identify security challenges impeding the small to midsize business community's decisions to implement or not implement needed and relevant security countermeasures, policies and plans and their ability to sustain them. In addition, it will layout a foundation for the argument that without affordable expertise they will remain “Targets of Opportunity” or “Soft Target” until such time the expertise and the understanding the needs is available to assist in the deployment of technology to support those plans. In addition, offer recommendations and insights to help a community bridge their current strengths and weaknesses based on observations and the potential vulnerabilities as a result.