Can your autoresponder do this?

Im in need of a couple every specific functions for emailing and thought there might be an autoresponder service that made it possible to do what I needed. So Im wondering if anyone knows if its possible to do the following with any specific autoresponder service or program thats currently available or even possible to have something made.

This is what I need...

1) To be able to enter emails manually and be able to send each address a different email ( perhaps set up different lists with each list containing just the one email )

2) Need to be able to set up automatic delivery of emails to these address on very specific dates, such as Jan. 4th, Feb. 6th etc. etc. ( and not have it follow a schedule according to when the address subscibed to a list )

In the end, I have about 15 different email addresses that I need to send 1 email to a month on a very specific date. Each address will receive a different email containing different content. I would like to be able to set this all up for like a year at a time and have it be set and forget. It must be able to work on its own whether my computer is on and running or not.

So it is possible to have something created to do this or is there something already available or can an autoresponder be made to accomplish this?

Thanks for any suggestions.