They really REALLY shouldn't start with Zero and then chronologically step back to the first game. That's going to be a rather jarring transition and they'll get a lot more out of the prequel if they've gotten acquainted with the characters beforehand. I mean Yakuza 0 is kind of a treat if you've been following these games for a while but kind of meaningless if it's your first one.
So, disclaimer, I haven't played Zero, obviously, and I'm comparatively a series newcomer (my first Yakuza was 5).
That said, I think a lot of long-timers might underestimate how possible it is to start off with a late game in the series and still manage to keep up. For me, even starting with 5, after a few hours it really wasn't too difficult to figure out who most everyone was and largely what was going on, at least as far as it was relevant to the story being told. Maybe a person would have a better appreciation and pick up on more small references if they started at the beginning, but it feels like I've seen a lot of people somewhat overstate how important it is to "play the old games for the backstory" to be able to enjoy the later entries. It's possible that Zero is a special case because it's kind of a weird prequel-that-assumes-you're-already-familiar-with-the-characters, of course, but I can't speak to that specifically.
Like other people have said, these games can be really huge especially if you (rightfully) do a lot of the side activities, and I think it's somewhat likely that they might only actually get through one or two of the games before tapping out. In that case, I would say that playing the more tightly-designed, modern, better-looking current-gen ones is preferable, even if it's perhaps not the best way to get a complete view of the long-running story.
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