Unless the guy knows what he's looking at, or someone with him does, he's playing Russian roulette with 5 chambers filled.
There are a lot of dealers in every Hemmings Motor News, if he just wants to browse & get some idea of what's out there.
As already said, most every dealer is merely marketing cars, marking them up to cover expenses, and know nothing about them.
I strongly recommend he figures out what he wants, does some research on his choice(s), and spends time carefully shopping.
I've seen countless sh*#boxes at dealerships, where better cars were available from private parties at same or less expense.
If he wants to hate his experience with the car, and the hobby, go ahead and charge blindly into it.
The dozens of old cars I've bought through the years have all been private owners, for those reasons.
I can think of only one that made it past my radar, and that dude was a skilled liar who seems to have disappeared from 2 Mopar forums he frequented.