Providing daily attention to clients (many clients)

I want to focus heavily on free 14-day trials. What is important is that this is integrated into the entire customer flow.
there is attention (as much as possible). I am looking for a structure in the software that provides easy insight into which customers have received attention and which need it. This brings peace of mind when this process is streamlined.
For example, daily check-in (see HubFit), results check, training check, and the ability for me to provide comments on what they have eaten. All clearly organized in a checkbox structure; this client still needs this attention:
Feedback on nutrition, feedback on training, encouragement, a compliment (etc.). Happy to brainstorm.