Publishing blog posts to multiple blog sites with Word: a test

I was testing out blog functionality with a coworker (@Nathan_Locke) and he asked an interesting question: Is there a platform available that will let you publish to multiple blogs at once. My first idea was Word. Fairly simple tool to use (although it writes seriously jacked HTML) and on the surface it appears as though it will publish to multiple blogs at once, or at least let you publish to one then publish to another several seconds later manually. Note: Blog posts to WordPress require images to be uploaded first.

So I’m going to give this a shot. But before I do that, I ran across this interesting Warning while registering my WordPress account with Word:

So I get the gist of what’s being noted here: since I’m not sending this via a secure channel there is the possibility of someone intercepting my username and password. Should I be leery of publishing content this way?