What I don't get is that serious webmasters really do not need companies to buy them little things like domains to make serious money. That right there is a big red flag.
If someone is going to make money with a program I really don't see why they need anything purchased for them like that, it just sounds silly. If they are an established webmaster and know how to work things, needing someone to buy them domains is not necessary.
edit: 50 unused domains.