When I send an attachment from OsX vs 10.4.3 with mail vs 2.05 to my hotmail I get 2 attachments in my hotmail. The first which is smaller is non readable. The second is the correct attachment.
It's because of Hotmail runs on Windows sever boxes. So in Mail select the menu item "Edit" and do in the menu select "Attachments" the make sure the item is checked for 'Always send Windows friendly attachments".