When you send the email you can request a delivery trace, and a confirmation of delivery. This will show where the email gets dropped.
It might be that Hotmail have added the domain he is sending from to there own block list, if so you will need to contact Hotmail and ask for them to allow mail from his account.
You can use the senderID system to help get around this (see
http://www.microsoft.com/mscorp/safety/technologies/senderid/default.mspx)