I’ve already completed Yakuza 0 and Yakuza Kiwami, am currently about 15 hours into Kiwami 2.
I fell in love with the franchise after playing Yakuza 0 and initially wanted to play each game chronologically at least up until Yakuza 7/ Like a dragon, but I keep seeing new games releases and spinoffs that look very interesting, such as Judgement, Ishin, and most recently Pirates in Hawaii.
With my full-time job and other adult responsibilities I can’t possibly hope to get to play all of them, else I’ll never catch up to the current releases.
Are there any titles you suggest I should skip? Are there any “absolutely must play no matter what” titles?
Extremely bare bones playthrough would be just doing Yakuza 0 and then 7. Those would give you an overview of the two main gameplay styles the series has to offer.
If you want to play more then you probably want to finish the brawler games first before moving on to 8 since it has spoilers for the whole series.
The Judgement games are also good so you might want to try the first of those to see if you like it. Story is completely isolated from the Yakuza games though so I’d investigate this at your leisure.