nHTML is a DLL written specifically for mIRC, which as far as I know, still works.
Here is the link to a modified version which quite a few scripters use. From Hotmail.com --
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To use hotmail for sending email, sockets alone wouldn't suffice. The method this thread has been talking about uses a method where socket scripting alone works, however theres been a bit of a snag with the TLS involved. Your suggestion wasn't ridiculous, just not practical in this situation. Using Hotmail via nHTML would be possible if one chose to go that route, though.
I believe using AIM would be the best medium for sending text messages, however. Because not all carriers support phonenumber@carrier.tld, and that introduces a limitation. AIM however uses SMS so it's compatible with all carriers. I'm not sure if TOC allows sending mobile messages, but Oscar for sure does.