Can't send email via outlook


I’m trying to send email using outloook. I’m using a hotel network, and my yahoo config for the smtp. When I try to send a message to myself, it just disappers – I never receive it, and I don’t get an error message. If I address an email both to my dreamhost email and my yahoo email, it gets sent to the yahoo account about 50 times, but not at all to the dreamhost account. Any thoughts?