It sounds like hotmail is eating the email at the top level of their spam filtering (before it gets to your junk mail). I've heard of other issues like this with hotmail.
Another test you can try is to open a shell on your server and telnet into hotmail's smtp server on port 25. Run through the SMTP commands for creating a message (just google "telnet SMTP commands") and see if the server accepts it. If it does accept it, but it doesn't find its way to your inbox, hotmail is blocking it. Only hotmail can give you more information on why they are blocking it.
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Martin
Windows System Admin.
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