OK it sounds to me like you're saying that your boss is being stubborn and refuses to move to anything standard and manageable, instead opting to micro-manage somebody into maintaining a giant MS Word document.
Am I far off?
If not, then here's what I suggest:
1) Get some server space on a host that lets you log in to the console and send e-mail from your host. The former should be pretty easy, the latter might not (ISPs dont like hosting people that might really be spammers)
2) Write a Word macro that Twit Jr. can click after editing the address list that tidies up the list, exports it into text, then attaches that text file to an e-mail and sends it to you. This is fairly straightforward; just use the MS Ofice macro recorder.
3) When it's time to send the newsletter, create an e-mail in a text file, then use SFTP or something to send that file and your latest address list to your server.
4) Log in to the console on your server and run:
Code:
cat email_list.txt | while read addr; do cat newsletter.txt | sendmail -s "Newsletter Title" $addr; done;
Sendmail (installed by default on most *nix systems) will be smart enough to queue the thousands of messages and send them as fast as it can.
5) Curse your Twit boss for not letting you use an appropriate mailing list service like Majordomo.
This should take you at most 10 minutes a day...but obviously it's not the right way to do it. This is why managers are supposed to say "please do this for me" instead of saying "do this for me, and
do it like this!.