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Reason I'm asking is that I've suggested to my older sister that she might like to give the Final Fantasy series a try as she played Super Mario RPG and didn't think much of it's plot and story compared to how much she paid for it. I can see what she was getting at as I paid the NZ $80 for it too, and with all the noise which I'd heard about it, I thought it would've been better than what I experienced.

I'm focusing on the early titles as I feel that back then the difficulty and expectations were "reasonable", unlike when it got to 10 and there were the challenges which came across as much as torture to me that I didn't even bother with them, like the Butterfly game and the dodging 200 bolts of lightning. Yes, I know that FF9 had the skipping rope game, but I knew all you got from it was a pointless key item so that could be happily avoided.

So having gotten all that out of the way, could you tell me if you think that this order which I came up with seems reasonable? I'm open to suggestions too, but I tried to rank them by easiest to hardest. This is based mostly all on the battle mechanics and the boss battles, but also taking into account the dungeons to some degree as well.

1. VII
3. VI
4. IV
5. I
6. IX
7. V
8. III
9. II

Your ranking sounds about right to me. All of the difficult challenges in later games are optional. You don't have to get and upgrade the celestial weapons in order to beat FFX, for instance. Nor do you need to breed a golden chocobo to go and get Knights of The Round to beat VII.

Older titles can require some grinding and I don't know if that qualifies as "difficulty", but it can get tedious. Some aesthetic choices can get in the way of enjoyment as well, such as the DS version of FF3 having the characters swing their weapons way too many times before the damage numbers show up.

That being said, it sounds to me like your sister was disappointed by the story of Super Mario RPG. If she wants the best writing that the FF series has to offer, I would recommend X (memorable characters and great love story) or VII (lots of suspense and psychological themes).
Guardian of the Description Thread
I'd suggest Xenogears, except it's story might be too complicated. It's also not a Final Fantasy title.

I cannot speak about the difficulty for the NES games, but, my approximation for difficulty of the other titles might be similar to yours? Maybe switch the positions of 9 and 5. I dunno. It's kinda difficult for me to scale these, because none of them are particularly more difficult than the others. Especially if you use cheats, or hack save-states. Which I absolutely admit to doing.
That seems like a spot-on ranking. III is kinda funny because its last stretch is probably why save points were invented.

Is your sister playing video games for their stories, though? She might be better served by reading a good book. It's also kind of funny that you exclude the later titles, because they were more story-heavy. IX and X might be the best compromise. The International version of X is better than the initial version, because the Sphere Grid was redesigned such that any character could take any growth path.
The reason I've decided to focus on the older titles was that they used either turn-based or the active time battle systems, both fairly easy to keep a handle on as opposed to the action system which has seemed to be the standard now. I know that Final Fantasy X is turn-based too but I'm mostly keeping it to the ones I know pretty much like the back of my hand. That way, if she ever does get stuck or needs a pointer, I can help easily. Also keep in mind that she plays the games on the Switch, so that cuts some other titles out too. Otherwise I'd be recommending Chrono Trigger if it was available.

The previous rpgs that she has played have mostly been the Pokémon main series, but as I said, she has branched out a bit trying Super Mario RPG. I just think for doable RPGs which aren't too difficult and having good plots and stories, the Final Fantasy series is a good way to get started. Also these days, the older games are good value for money for what you get out of them. Especially if you haven't played them before.

Anyway, thanks for your responses. I'm glad that my idea of the difficulty of the titles seems about right.
The PS1 Final Fantasy's problem is that they were during the era when battle animations were absurdly long. People don't have that kind of attention span anymore, and even going back with our nostalgia-tinted glasses requires an effort. For that reason, I would recommend FF5. The gameplay is consistent, not too difficult, the job system is fun, and the cast is likable enough. The plot isn't much, but it does have it's moments and this is babby's first game so who cares. If she wants to play more FF after beating it, cater to her tastes then.
I start with FFIX, because this was my first Final Fantasy when I was a child.

1. Final Fantasy IX
4. FF IV
5. FF V
6. FF I
7. FF II
8. Final Fantasy VI
(Some and especially the last dungeon were hard in my opinion and I played it first time, two years ago. Its a great game.)

Final Fantasy 3, I never really played. D:
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