Well, I think I found it. I never used Automator before but I did tonight and it seems to do the trick much more easily than anything else I found. Drag on two Mail actions (New Mail Message and Send Outgoing Message), write the message, save as an app, schedule a repeating iCal event, set the alarm to open the new app, and that's it.

Thank you for posting your answer. I was looking for something similar and this is a godsend.

I set it up to email reminders of needed weekly reports. iCal does this fine if the reminders are to me, but not (yet) to others.

I am trying to help my teenage son organize a bit and he has been having a hard time remembering to look at his assignments or next action list. I used this to set up an automated sms message to go to him at a specific time every few days to get him in the habit of checking his lists. Basically the only thing I changed was the email address was 5555555555@messaging.phonecarrier.com (each carrier is different and you have to look that up) - works like a charm!

Thanks
em :)