I think I came out of this replay with a bit more of a positive opinion of this game, but I still don’t really get why the fandom seems to love it as much as it does. Ryuji is a pretty good rival, even if he doesn’t have the depth of some later LAD antagonists, and the first half to two-thirds of the story does a pretty good job of building up tension and developing Kiryu and Sayama’s relationship (which is alright, but suffers from Sayama being a victim of early RGG female character writing), but the game loses the plot a bit in the final act and devolves into a bit of a mess of twists and betrayals over character- it reminded me a bit of Yakuza 4 in that regard, which is not a good thing at all- and most of the other villains are kind of weak. With the Jingweon in particular, RGG has always had a problem with depicting foreign crime syndicates as a lot more one-dimensionally villainous than and lacking the nuances of the yakuza while also showing very few Chinese and Koreans living in Japan without gang connections (one of the few things I liked about 4 is that it actually made an effort to highlight the latter and 7 and Lost Judgment looked like they were finally starting to get away from the former only for Infinite Wealth to partially go back to business as usual), and with how prominent they are in the story this is by far the most egregious case with the game frequently taking opportunities to go on about the Jingweon’s extreme creed and lack of humanity compared to the yakuza among a bunch of other questionable at best things (not helped by one of the first scenes of the game being Yuya yelling about not going to hand the town over to "foreigners" that have nothing to do with the rest of the game). The ending also just kinda sucks, all I'll say about it without going into spoilers is that I’m really glad Infinite Wealth finally decided to deconstruct and call out that side of the character as a Bad Thing. Overall I don’t straight up dislike this game, but I do definitely find it weaker than its reputation suggests and I don’t understand why some people give 3, 4 and 5 grief for some of their dumber aspects and love this game when a lot of them can also be found here.
As for how the PS2 version compares to the remake, let’s just say it’s a much more even fight than the first game. I do think the overall presentation of the PS2 version is better and there are some other things to complain about with K2 (losing Shinseicho and some other content, very questionable licensed music usage though to be fair the original’s isn’t great either, having later-period RGG’s usual forced minigame tutorials break up the main story pacing), but at the same time there’s nothing that’s damn near game-ruining like Majima Everywhere, K2’s localization is better, the soundtrack (another extreme point of contention) is IMO a matter of preference (K2 does have a bit less variety in battle music, but at the same time it also does give special themes to some fights that didn’t have them originally- the first part of the finale in particular loses a lot of gravitas when it’s just using normal encounter themes you’ve heard like 10 times before) and I think Yakuza 2’s battles adapt a lot better to the circa-Y6 Dragon Engine than Yakuza 1’s did to the Yakuza 0 engine (plus they didn’t shoehorn in any dumb gimmicks like Kiwami 1 did). The basic combat of the original holds up a lot better than 1’s, but it’s undermined by the boss fights basically being a reminder of everything I didn’t like about pre-Dragon Engine LAD combat and having some really unforgiving QTEs- people complain about Kiwami 2 being too easy, but IMO original 2 isn’t more difficult in a fun way, just an annoying way. I find it absolutely baffling how Kiwami 2 is much more often considered a worse remake than Kiwami 1 among a lot of older LAD fans- personally I’d consider K2 a sidegrade at worst, unlike K1 which I think makes a mess of the original game.
As for how the PS2 version compares to the remake, let’s just say it’s a much more even fight than the first game. I do think the overall presentation of the PS2 version is better and there are some other things to complain about with K2 (losing Shinseicho and some other content, very questionable licensed music usage though to be fair the original’s isn’t great either, having later-period RGG’s usual forced minigame tutorials break up the main story pacing), but at the same time there’s nothing that’s damn near game-ruining like Majima Everywhere, K2’s localization is better, the soundtrack (another extreme point of contention) is IMO a matter of preference (K2 does have a bit less variety in battle music, but at the same time it also does give special themes to some fights that didn’t have them originally- the first part of the finale in particular loses a lot of gravitas when it’s just using normal encounter themes you’ve heard like 10 times before) and I think Yakuza 2’s battles adapt a lot better to the circa-Y6 Dragon Engine than Yakuza 1’s did to the Yakuza 0 engine (plus they didn’t shoehorn in any dumb gimmicks like Kiwami 1 did). The basic combat of the original holds up a lot better than 1’s, but it’s undermined by the boss fights basically being a reminder of everything I didn’t like about pre-Dragon Engine LAD combat and having some really unforgiving QTEs- people complain about Kiwami 2 being too easy, but IMO original 2 isn’t more difficult in a fun way, just an annoying way. I find it absolutely baffling how Kiwami 2 is much more often considered a worse remake than Kiwami 1 among a lot of older LAD fans- personally I’d consider K2 a sidegrade at worst, unlike K1 which I think makes a mess of the original game.