You can Add new Checklist Tasks on a schedule, e.g. every day, specific weekdays, and specific days in a month.
In contrast to the Recurring functionality in Tasks itself, you don't have to complete the task for a new Task to be created. In addition to that, you can also Cancel the previously created and still open Tasks.
To start creating recurring Tasks for a record, just manually or automatically Add Checklist Tasks for the record. Note that recurring Tasks are not created automatically for new records.
You can stop creating recurring Tasks by de-selecting the Create Recurring checkbox in the Checklist Instance.
In the Checklist define the Recurring information:
In this case, a new Checklist Tasks are added every Monday, Tuesday as well as on the 16th and the last day of the month (if the day is later than the last day of the month, the task is created on the last day, e.g. on 28th Feb).
In addition to this. the existing open Checklist Tasks from previous executions are set to the status of Canceled - see: Task Completed vs Canceled
To automatically create the checklist tasks, schedule the Apex class RecurringChecklist
> Setup > Apex Classes -- click Schedule Apex
Set the schedule up to run every day at some time in the early morning (it needs to run during the day, not in the evening of the previous).
Set the End date to the latest date possible as when the schedule expires, you will get no message. You can manage the scheduled apex classes in: > Setup > Scheduled Jobs
You'll receive an email with details for which records and Checklists new Tasks were added.
Manual Start and Check
In the Checklist, select the action Recurring
If you click "Recurring', you will see the instances (i.e. records) the new Checklist Tasks will be created and a message if you can start the batch (i.e. if it were to create Checklist Tasks).
You will only see records for which you previously added checklist tasks - i.e. it will not automatically run for all instances - you need to run it at least once for a particular record (manually or automatically).
After starting the batch, you'll receive an email with details for which records and Checklist new Tasks were added.
Exclude / Stop / Start recurring tasks for a particular record
When the checklist tasks are added, an instance is created for that record. The last instance created has a flag: Create Recurring
If you de-select the flag, no future recurring checklist tasks will be created. You can also select the Create Recurring checkbox to restart creating recurring tasks.