Intelligent tutoring systems (ITS) can help students learn successfully, yet little work has explored the role of caregivers in shaping that success. Past interventions to support caregivers in supporting their child's homework have been largely disjunct from educational technology. The paper presents prototyping design research with nine middle school caregivers. We ask: (1) what are caregivers' preferences for different prototypes incorporating data-driven recommendations into their math homework support? Integrating caregivers' preferences, we then ask: (2) what are caregivers' perceptions when interacting with a prototype of an intelligent chatbot tool to support students' homework? We found caregivers reported feeling comfortable integrating AI into their practices and appreciated chat-based support for understanding content and effective ITS use. Our results highlight the affordances of ITS data and AI to assist caregivers who would otherwise not be able to support their child's homework, paving the way for more effective and equitable mathematics learning. [This paper will be published in the ISLS2024 proceedings.]