I guess it depends on the reason(s) you play the games. If one wonders how the series changed over time, it's not necessarily a bad decision. As for me, I had the time and I prefer to tackle series (whether it's games, books etc) chronologically. But like I said before, I-III are too generic to really matter but if one has nothing better to do...why not?
I'm certainly the chronological type of guy too, yeah. We'll see how I enjoy those games. By the way, I'm interested in researching trends, seeing the evolution of games / the genre, learning more about those 80s consoles, appreciating the pixel art and the music, etc. Approaching things this way goes beyond focusing on *just* the particular, if you know what I mean. So there's lots of enjoyment to be had (for me) even if the actual game/gameplay is average.
It always depends on the person but at some point one has to look for other things to draw out of a game. If one has played as many games as I have, it's always a "been there, done that". And while gameplay-only works fine if you are a kid/younger, at some point, one will grow tired of it, unless one can stomach inane repetition (I can't). So there has to be something else, like a somewhat unique story, interesting characters...or maybe one plays it from a more removed perspective, like looking at the trends, changes etc that you mentioned. And that certainly works for shorter games that don't take 50 hours but even then, at some point, one might not be able to stomach it any more. Obviously, it also depends on the frequency and how much one plays per day. In the case of Final Fantasy, 4+ is fine, as the themes, characters and the story can carry it decently enough. But for the games before that, it's more difficult.
I guess to make my point more clear, one would have to look at the Fire Emblem Series, or the Super Robot Taisen one. Those games take a long time to complete, are generally low in the story-to-gameplay ratio and are really easy. So if you played like 3-4 of them, it's difficult to continue doing so, especially if the story is similar to previous games (in the case of Super Robot Taisen). It's also why I have no love for Fallout Tactics: Brotherhood of Steel, as I didn't see a point to it. I've had that gameplay in games before and those offered story at least while the Tactics game was just drab. Though, to be fair, one of the main issues is the time frame of playing these games. Originally, they were released then and a year or two later, another game followed. So, ideally, one played those games with a buffer in between and was able to appreciate the difference more, also in connection with other games released around that time. Playing games now, with knowledge of the future and possibly a lack of such a buffer drags the experience down, unfortunately.
That being said: The Japanese gaming scene is generally the most interesting one, in my opinion. As a European, I know about the uniqueness of German, French and British games and I obviously know the general American style but the Japanese have Western ideas presented in their unique Japanese way and then also completely unique Japanese experiences. They had their own computers, their focus on the strengths of those which were different to the ones here, the stronger tie-ins between the rest of the media and games, an often more professional way of doings things due to companies unrelated to gaming branching out into it, a way stronger doujin (aka indie) scene than what we had here etc. Though, in the last couple of years I've soured a bit on it due to Western "journalists"/know-it-alls shining more light onto it which invited casuals to take notice of it...which is a bad thing. The expansion of retro-game-collecting was another blow to the whole scene. To post an anology: We went from watching and admiring the field to this:
https://www.theguardian.com/world/2...-tulip-fields-barriers-tourists-selfie-takers
romhacks.
