It's generally why I prefer to play games in release order instead of chronological order. Prequels are almost always weirdly executed in gaming, because the prequel will often feature refinements, mechanics, and polish that the "sequel" does not.
I only played a little bit of the original Yakuza when it released on PS2, so I was excited to play Yakuza Kiwami. I beat it, and loved it, and then went on to Yakuza 0 (which I believe I'm only in chapter 7 or so at the moment). For me, it was more enjoyable experiencing them that way because 1), I was able to appreciate Yakuza Kiwami on its own merits (it's still a fun beat-em up with an entertaining story), 2) It was really enjoyable to see the 80's version of the district I spent so much time roaming around in Kiwami, and had grown rather familiar with, so it was really fun, and 3) The tighter mechanics, polish, and expanded gameplay/narrative wasn't as jarring to me, because I played it after Kiwami.
It's going to be interested when I get to Kiwami 2, however, since it's not going to have some of the features that I've grown accustomed to with 0. I hear it's the best game in the Yakuza series anyway, so I'm not terribly concerned though.