It's not hard at all--- I have treated my sister to about five Marriott points-stays in the last few months. Call the main Reservations number; they will confirm the availability and make the reservation, then they will transfer you to the Marriott Rewards desk to debit the points from your account and issue the certificate. Your brother will need to present the certificate when he checks in; I asked them to mail it directly to my sister and each time it arrived (no exaggeration) the very next day via DHL. We've never had a problem!