I ended up using a program called Serial Mail for the first mailout I did. I’m really hoping it works, as there isn’t really a way to tell if it has or not. It’s currently sending them as I type this.
I really think I’ll end up rolling my own - there’s some limitations as to the system I used (a typo/bug means I can’t get people’s birthdays!), and I really think I can do better. I think I’ll write my own templating interface, rather than use a Draft (although, this is a good idea). And it just uses AppleScript calls to do all of the generation - I think I may try to hook straight into the APIs.
Which reminds me - I came across someone who mentioned it’s possible to make ‘proper’ custom fields in the Address Book Database - which wouldn’t be accessible through the standard application, but would allow greater flexibility. Like to define a field as only being able to have a particular value, such as a Coaching or Referee Level, or Gender.
A custom program that can work with custom fields, and do mass-mailings. Something to do in the next holidays.
I wonder how long this thing is going to take to send all of those 146 emails?
If you still want a copy of that script, let me know. If you did email me, it may have inadvertantly gotten caught by my spam filter.
12 hours, 40 minutes after the fact.