This pilot study addresses the need to clarify specific developmental vulnerabilities and strengths that characterise children living in child-headed households in comparison to children living in adult-headed households in equivalent impoverished communities. Samples of 10 each of these two categories of household were randomly selected from impoverished communities around Pietermaritzburg, South Africa (involving a total of 22 children from a child-headed households and 41 from an adult-headed households). Fourteen child-participatory, quantitative and/or qualitative measures were investigated over six indicative themes. Differences between the child-headed and adult-headed households were statistically or thematically analysed as appropriate to the data collected. Specific areas of vulnerability in the former households were access to institutional/social services, income (cash or kind) and resource generation, unresolved grief, lack of attainable long-term goals, poor self-worth, and poor internal locus of control. Specific strengths of children in those households were demonstrated in social networking, time and money management, and family interactions.