In Contacts Live Mail you have the option of scheduling future dates and times to create an automatic 'Drip System'.

 

While this may seem a little monotonous, it really only takes a few minutes to setup up an entire year's worth of monthly or even weekly email drip system.  Here's how...

 

In the “Send Mail” form select “Send Later” radio button (instead of the default on “Send Now”) and indicate sending date and time in future:
In Contacts Live Mail you have an option of scheduling date and time in future when you want your e-mail to go out

 

Your message receives Pending status and stays in your mailbox until it is sent out at indicated time.  That's all there is to it!