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It has been so long since I'm been involved in that I don't really have any specific advice.
However, at a much higher level I would say to make sure he is involved in and actively participating with the process and that you're not just doing everything for him. As much as it may seem that it is something that needs to be done even if he won't invest himself, college is something you have to have a personal drive for.
And if he doesn't even have enough of one to work out where he wants to go and how to go about paying for it then he's going to quickly fall under the train when he actually gets there and finds out that nobody makes you go to class, that the instructors don't really care all that much if you pass or fail (if you care, they'll care, but if you don't care enough to work at it they generally have better things to spend time on).
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