Challenges associated with ADHD affect children's daily routines and response to environmental stimuli, and support from parents is helpful in managing and overcoming behavior regulation challenges. Positive reinforcement is increasingly integrated into family technologies for teaching regulation skills, but typically support specific co-located activities. To better understand how technology can support co-regulation within families with ADHD children, we deployed CoolTaco, a smartwatch and phone system to support collaboration in creating tasks, gaining points for achieving them, and redeeming rewards. Ten families with ADHD children used CoolTaco in their daily routines. By qualitatively analyzing family interviews and usage logs, we find that smartwatches can help provide pervasive regulation support to children, but the division across devices and parent-child roles interfere with developing independence. We discuss how technology should support co-regulation while also fostering future self-regulation, such as by guiding children in goal setting and helping them reflect on progress and achievements.