This study explores how generative AI (Gen AI) painting systems can enhance social connectedness between young adults and children who live apart. We designed a system that transforms personal sound recordings, emotional prompts, and photos into visual artworks, and investigated how different levels of parents’ related information involvement affect young adults’ connectedness with their parents. Through a within-subject pilot study with three participants, we compared three modes of AI-assisted visualization, ranging from different levels of human information involvement based on Gen AI support. Our findings suggest that greater personalization, particularly when incorporating emotionally meaningful photos, can elicit stronger feelings of connection. However, more involvement does not always produce stronger connectedness; effectiveness depends on perceived emotional intent and contextual relevance. We conclude with design implications for future human-AI co-creative systems that aim to foster social connectedness in long-distance families.