I would buy him a small bike and then let him work to get a Harley. You can pick up a nice yamaha or honda pretty cheap. If you are going to flog a bike and dump it it may as well be a cheaper one.
I've found a lot of Sportsters around for less than $4k, and many of them for less than $3k. Granted, they were 883's, but good for him. I've been looking for a cheaper bike for him, but it's hard to find anything decent without spending $3k or more.
