Because he has changed schools before means he will change schools again... That's quite the leap. While I don't necessarily disagree with the conclusion, just don't believe it's that simple.
You're last two posts have drawn a pretty firm tie between sales and recruiting. While I believe there are similarities and you can definitely tie successful salesmen traits to successful recruiters, I think you have to stop short of saying the scholarship is a "product" and then should run your recruiting strategy per the same guidelines most sales/marketing strategies are run.
To answer your question at the end of your post, incent him. However, as most incentives often incur, there is a drawback. You always must ask, what if you get what I "want"? What if he signs a bunch of early recruits because that's what you want? What if they aren't the kind of recruit he should be landing, but just someone to sign to get the incentive? Was it worth getting that early recruit?
I don't think Kill is a salesmen and I don't think scholarships are a product. So as someone who runs a sales company, I agree with your post, I don't think its as relative as you are making it out to be.