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I've been running my main newsletter, the Webmaster Times, for a few years now. Its not hugely popular, but the main reason I run it is because it 'forces' me to create new content for my site (It's difficult to get motivated sometimes!). Unfortunately I haven't sent it out for a few months because writing it takes quite a while. Its mainly just a single article on something related to site building, but the article is always unique to my site. I host it myself as it's not very big.
The second newsletter, Free-Webhosting Update, is one I am quite proud of. When designing the newsletter for Free-Webhosting.info I realised that each month I would simply be writing a review of a host and posting it on the site and in the newsletter, so I combined the two. The newsletter is now fully automated.
Each month I go to a PHP page which generates the newsletter based on the database for the site. It puts in the latest review, the newly added hosts that month and some statistics (e.g. top 10 hosts) and then sends a copy to me. I then check my e-mail and have a link which I click which takes me to another script which sends the e-mail to all the subscribers individually, and sends a copy (with the subscriber list) to me. The newsletter is then stored in an archive.
It's certainly saved me a huge amount of time, and there's really no reason why it shouldn't be fully automated. I could set it up as a cron job and have it run and send automatically once a month. I do like to check things first though.
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