(Legitimate) Mass Email

I’m in a situation where I need to send out large numbers of emails - now, settle down, I’m not talking Spam! Rather, I am the _Member Communication/Liason Officer _for a sporting organisation, and need to send many emails out to either a subset of the community, or in some cases, the whole community. I’m thinking about different methods to streamline my communication processes. I think I have a few options: Mail.app and Address Book. Using the Groups feature of Address Book, I can send out emails to the right combination of people who need to receive them. For instance, I can have a Men’s Open group, a Women’s Open group, a Juniors group (not really required anymore), a coaches group, a committee group and so on. This should work pretty well, but will require me to have all of the up-to-date information in Address Book. Not necessarily a bad thing, but I need to ensure that Word/Excel can use this as a source (we have some custom generated forms that need to be populated), or custom-generate some sort of interface solution. Perhaps I should add extra fields to Address Book, and use that as my database. The other option is to go the whole hog and create a Database (MySQL, or something similar) that I can use to store the data in. Ideally I’d like to have an online one, as then I can access it from work if I need to. Otherwise, I’ll only be able to send out emails and so on when at home. That is the big disadvantage of the first solution. The other possible disadvantage of this method is that with a large number of emails, I may look like a Spammer. Which brings me to the other option - a dedicated mass-emailer. Of course, this itself may make me look like a Spammer - emails may be rejected just because they use a particular X-Mailer: header, or something strange like that. A better solution might be to custom-roll an AppleScript solution that generates individual emails from a list. This could be a goer. Kind of like a Mail-Merge, but and Email-Merge. I’d like to be able to do this as an Apple Mail plugin, but a stand-alone app might be easier. Then I can write it in AppleScript Studio. I’m liking the sound of this: extend Address Book so it has (for instance) Coach, Referee and Selector fields (for an indication of NCAS/ATA Accreditation level) and so on, and combine this with some fancy AppleScripting to allow for personalised emails, and generation of reports. Next week, maybe. When I’ve finished writing all of the Year 12 SARs.