Mental health struggles wax and wane, yet clinical and wellness interventions typically operate separately, causing frequent breakdowns at care transitions. We explore reinforcement learning (RL) as a means to build digital health systems that deliver clinical and wellness interventions proactively, as part of a coherent care journey. We ask: what complexities does designing such a system involve? We built a contextual bandit that dynamically selects journaling prompts from clinical and wellness repertoires to optimize for an overarching health goal (sustained journaling) and deployed it in a four-week exploratory study (N=38). We found that, first, many benefits of RL-optimized intervention sequences appeared only after interventions ended, raising the question: Should systems that offer coherent clinical-wellness care journeys include stepping-back periods? If so, when and how? Second, participants most engaged with RL-generated interventions deepened their engagement over time, while those most engaged with a constant intervention tended to burn out and drop out later. It raises the question: When should a system blending clinical and wellness interventions reduce intensity to prevent burnout in versus sustain it to maximize treatment gains?