Then he doesn't want a vintage bike. You said he has money. He'll need it if he's hiring someone to maintain it. Bottom line, heed the advice above. It's good advice. I recently bought an 09 Bonneville for less than half of its new price. Reliable as a brick, fun to ride and he'll like this part...lots of compliments while fueling up.
He can pick up an old airhead for $3k, then quickly spend $3k to dial it in. When all done, it'll be worth $3k. Encourage him to buy an old MGB if he wants to get stranded but not killed. Here's my 09 Bonnie. The best solution if he must own a bike. BTW...does he know how to ride? Have gear?