I'm glad you're not ready to give up Koya. It seems possible to me.
If anything, it looks like you'd have to implement an https (secure http) and post to the hotmail cgi script. Winsock and Inet should be able to do the POST, but I've never tried https with them.
Look at the following FORM ACTION:
<form name="passwordform" action="https://lc3.law5.hotmail.passport.com/cgi-bin/dologin" method="POST" target="_top" >

But hotmail can reject your POST based on CGI environment variables that are set (exposing the fact that you are using vb instead of a browser).