We've been currently looking for a way how to deliver reminders on a particular schedule, which is issue specific. We have added custom fields ReminderDate and ReminderFrequency (daily, weekly, bi-weekly, monthly). Based on ReminderDate we look for issues using JQL search and send a reminder to assignees - all team members are subscribed to the filter. We were hoping to update ReminderDate field with a new value according to value of ReminderFrequency using JIRA Automation plugin. This way we would be able to remind assignee on regular basis. Unfortunately this operation seems to be currently unsupported for date fields 
Can you please help me with our use case? How to accomplish this with JIRA Automation plugin?