Public school districts across the United States have implemented school choice systems that have the potential to improve underserved students' access to educational opportunities. However, research has shown that learning about and applying for schools can be extremely time-consuming and expensive, making it difficult for these systems to create more equitable access to resources in practice. A common factor surfaced in prior work is unequal access to information about the schools and enrollment process. In response, governments and non-profits have invested in providing more information about schools to parents, for instance, through detailed online dashboards. However, we know little about what information is actually useful for historically marginalized and underserved families. We conducted interviews with 10 low-income families and families of color to learn about the challenges they faced navigating an online school choice and enrollment system. We complement this data with four interviews with people who have supported families through the enrollment process in a wide range of roles, from school principal to non-profit staff (“parent advocates”). Our findings highlight the value of personalized support and trusting relationships to delivering relevant and helpful information. We contrast this against online information resources and dashboards, which tend to be impersonal, target a broad audience, and make strong assumptions about what parents should look for in a school without sensitivity to families' varying circumstances. We advocate for an assets-based design approach to information support in public school enrollment, which would ask how we can support the local, one-on-one support that community members already provide.