On a monthly model, you want users to keep renewing. However, users want their insomnia to be cured quickly.
What about flat pricing instead? 7 days free to get over the pricing friction, $150 to purchase a license to the customized program, possibly with a fairly weak warranty (minimum 10% improvement in sleep time in the first 6 months or your money back.)
Now your incentives are the same - get them "fixed" as quickly as possible and off the platform (and obviously upselling them on affiliate/related stuff if happy.)