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I never did play much of FF2, it is different, one I wasn't crazy about.
Final Fantasy I is a classic RPG that is easy to understand, and while it's not particularly amazing at this point, you're also very unlikely to dislike it.
III is my least favorite. The job system leads to all kind of gimmicks with bosses and different areas of the game where they want you to change your entire party to specific jobs. You don't *have* to do this, but it makes already annoying areas even more annoying.
You'll likely figure out if you like the game very quickly, as the gimmicks start almost as soon as you leave the first couple villages.
So my thoughts out of these 3 is that Final Fantasy II has the best story and gameplay, but many people will tell you it's their least favorite because it doesn't function like most other traditional RPGs.
Final Fantasy II is... VERY weird for the series. I think it's a great game in its own way if you're down to clown with what it's aiming for, but in terms of how it actually plays in practice, it's... not very representative of the series at all. Story-wise, it IS very evidently a NES game (I mean, they all are), but I think it's pretty darned competent within those restrictions! The majority of the named characters contribute meaningfully to the story in one way or another and have clearly defined places in that story and world, and the villain, while simple, is among the most competent in all of Final Fantasy and really lends the story a great sense of genuine urgency and dire stakes.
Final Fantasy III, while the Pixel Remaster is actually the only version I can't yet speak to, is very much centered around its Job System. Unlike later iterations in games like Final Fantasies V and Tactics, nothing but HP growth is carried over between classes. As a result of this, the game is EXPECTING you to be changing your classes on the fly to adapt to new challenges, and certain areas are balanced such as to put STRONG pressure on you to do this, which isn't a decision that's going to jive with everyone. It also means you shouldn't be too eager to sell old weapons and armor when you change out of classes that used it, since you may find yourself changing to classes that need that gear again down the line and you don't want them to be left naked and unarmed. That said, III is, in my opinion, also a very good game, and it's great fun coming up with wacky strategies and team lineups! FFIII also has a much more defined story than FFI, but not quite as much as FFII. Where FFII is a grim story about the struggles and tragedies of resisting imperial subjugation, FFIII is a much more lighthearted adventure through a colorful fantasy world. It has an almost dreamlike quality to it, actually.
I ultimately can't really speak to which one would be the best for a player new to the three NES installments to start with; that's something you'll ultimately have to decide for yourself. They're not connected story-wise any more than any other numbered Final Fantasies, so there are no worries with playing them out of order. My advice would be to start with the one that's closest to what you're already familiar with, or that you think you'd have the easiest time adapting to, since that's the installment that will likely make for the best "bridge" entry for you into the NES Final Fantasies.
I'm interested though, what in particular makes FF2 so strange? If I beat FF1 I might just buy the collection and try this one out as well
I is a step-up but it wears its influence on its sleeve; Dragon Quest meets Dungeons & Dragons. It's actually a small game but it's fairly padded with grinding and maps that are full of empty space. Much more approachable than II.
III is a massive improvement and easily worth recommending alone. It's basically a sequel to I but better in every way. The score is phenomenal, the dungeons are tighter and more linear, the scope is huge and there are three times as many places to visit, you have more options in combat, there are actual sidequests, the difficulty-curve is smoother, and there are countless setpieces (You can shrink in size to access new areas, you have an airship that aids in combat, there are foes that split in two if not dealt properly). Basically there's a ton of flavour and ambition. It feels like a SNES game that came out before the console did.
The pixel remaster also remedies the notorious lack of saving making this an easy-to-finish title.
And most importantly there is no level/exp system, instead taking on a 'use it to raise it' deal. It's a bit of a hit and miss especially because people can be used to just standard leveling systems.
One can argue that it's stat raising system just makes the game a SaGa prototype.
Out of the three NES-era titles currently available for the PR Collection, if I had to recommend one--and if we're talking between a balance of story, gameplay, etc.--then Final Fantasy 3 is probably the best choice. It also offers the most replay value thanks to its introduction of the Job System where it makes the game have a more dynamic experience/challenge. Besides that point, FF3 gives you the polished, addicting gameplay and challenge of FF1 without the annoyances and predictable narrative of FF2.
However, while the PR version definitely feels like the "definitive" experience, there are some aspects of the DS/3D remake that might be more to your taste. For starters, the characters actually have names and simplistic backstories/personalities beyond the nameless orphans in the PR/NES version. Second, some jobs are tweaked to be more interesting as well as unlocked earlier in the 3D remake whereas the PR version keeps the jobs aligned with the NES era--but they fixed the glitches/bugs with those classes, of course. Although, from my experience playing both versions, the 3D remake is way, way more difficult for newcomers, but the PR version is no pushover either.
Whatever version you pick, I haven't been forced to make my party into one optimal loadout based on the upcoming boss. I may have changed one or two characters to be more practical like the Scholar for that one boss who changes his weakness, but I won the so-called "4 Dragoons Only Rush" boss fight with one Dragoon and three other classes on support/offense spells. If the PR version fixes the problems with the Crystal Tower endgame--or at least makes it way more forgiving--then that alone would make the PR version the best version in my book.
Although, if you just prefer to have a decent narrative in a JRPG, FF4 / FF6 are more likely up your alley rather than the first three games.
The PR version of FF3 is way, way more forgiving and open to suboptimal classes compared to the DS/3D remake. I'm still using my Red Mage all the way from the beginning of the game right after getting the third airship (or after the Earth Crystal)--and I'm only around Level 23 for my party. Only time I swapped him out was to have a Scholar for the boss fight with Hein, and it suited him enough in looks and function.
Proof in the pudding: https://steamcommunity.com/sharedfiles/filedetails/?id=2563873747
FF1 is classic, smooth, and concise. Like someone else said, that third act might become a tad repetitive, but by then you're already hooked into the fun and enjoying the adventure, and you won't mind finishing it. And the last bit of the story is a tad interesting with the final boss and everything. I'd prefer not to spoil anything.
FF2 is actually underrated. Nevermind what people keep saying about the leveling system. It's quite simple really: If you play normally and don't put too much thought into it, then naturally everything you need to increase will automatically do so. Just have fun doing a variety of things in your playthrough, and your stats will raise accordingly. They made the GBA version easy, and I assume the same is the case with this new one. The story is its stronger attribute, and the game even has a bit of a somber tone at times. How easy they made it should make it pretty easy for you to get through. The fourth character in your party comes and goes up until a certain point (if I recall correctly), but that only makes matters interesting.
FF3 is a grand experience - the best of the three. It is an epic adventure that really maxed out the NES's capabilities. Like someone else said here, it is dreamlike in its world as it unfolds like some kind of fairytale. The NES version of 3 was even more impressive than the GBA remakes of 1 and 2. You really can't go wrong with this one, whether you play the NES original or this remastered edition. You can see how this game served as the blueprint or stepping stone for what would go on to become some of the grandest stories of all time in FF4 and FF6. I think you should save it for last. The entire series is a blast.