I do agree with Joel, if its not going to be a win-win the broker has no incentive to hold your license. If all you're doing is using the resources of the broker and not contributing to their bottom line then its not a win-win. I don't do as much leg work as I really should to get business (I own two other businesses in town) but I am out there talking real estate and drumming business up. I'm more of an agent then investor, although I am both, and that's a win-win.
KW is a great agency and I love the people. I would highly recommend them once he's licensed assuming he wants to be both, investor and agent. We all have people we know and people buy and sell homes all the time. Might as well make money with your license. I would recommend approaching all potential "deals" he comes across with the utmost integrity. If its something he's asked to list and wants it for himself he has the duty and responsibility to tell his broker and the homeowner. Trying to slip anything under the table will not only open you up to problems it will cause you to loose your integrity and the peoples trust.