If he always wanted a Harley, he's not going to be happy with anything until he gets one. Some of my best friends ride Harleys and couldn't imagine owning anything else whether it's better, cheaper, or not. I must have 10 or 12 friends with Harleys and none have buyers remorse. Some think about their "next" Harley. I'm the only non-Harley in the group.
Personally, my favorite bike was a Triumph I had in '71 and I always wanted another one. I never wanted a Harley and still don't. I've never had trouble buying what I want - no matter what other people say. I've also had a Mac computer since they came out in '84 - never really cared what other people use or feel they have to have. I do get tired of people telling me what I should buy.
Ease up on the guy. He probably has the bike of his dreams.