I am trying to find a way to automate follow up emails 2 weeks after a purchase date.

I am entering the purchase date in as an activity as the purchase date = event date that we provided services on. We use a scheduling system so this is done manually. The due date for the task is the date of the event.

At this point I have set up an automation to email the contacts which have this task on their profile 14 days after the due date of the task.

I need to find 2 things

(1) how to test this functionality and make sure it works. I entered myself into the system and put a task on there 2 weeks ago, but do not know how to force the email to go through. I would prefer to make this email template available under contacts as well but find it redundant to have to duplicate the template for this purpose. I cannot clone the template and save it under contacts; I would need to start over and recreate it under that module.

(2) how to batch email people whose events were greater than 14 days ago. I do not want to put incorrect data as I want to keep the event date accurate. Because of a system conversion, our follow up process was on hold for several weeks. This means that anything I entered in with an event date of > 2 weeks ago will not be caught in the automation. Is there a trick to the automation that will cause these to get caught and emailed? Or is there a way to select multiple tasks and have them emailed at once? 

Because the template is under the Tasks module, I cannot manually send emails to Contacts under the Contacts section nor when I have the Activities area open.

Suggestions for a better method to do this follow up process are welcome. I have searched the forums regarding the email template but did not find the answers I was seeking.

Thank you!