OK, I breezed through V(thankfully). I'm writing
spoilers to V from here out.
Had to be the single most callous entry into the series, at least story and character wise. At one point, to advance the story, you get a ship, travel across the ocean just to crash it, find a chocobo, fly the bird back to the people that gave you the ship. They don't care and tell you what you needed was there anyways.
The first world felt like I was playing a FF parody. You're changing mode of travel so often they partitioned the world in a multitude of different ways, which gave a real odd feeling to the world. Get a ship, lose it, get a dragon, lose it, get a chocobo, lose it, get a ship, crash it, get a chocobo, abandon it... or something. The second world was a little better, but the plot in both was still basically the group wanders with no clue what to do while some bizarre event helps them. If the game had ended at the second world it might have been a better game, by the time the third comes you just went from end game feeling to having to complete a bunch of random dungeons for no reason. ...and the final dungeon was awfull, if you want the third part of the game to matter to me you have to make me care about the world. The whole third world was just so blah.
The characters, no development, and the frequent snarkiness just made the group seem absurd. The only thing I learned about Reina is that she's a suicidal princess. The Galuf to Krile switch was silly, and Krile got no development until after the game finished(although I guess the ending varies depending on the final fight. The only significant revelations were in lineage, which was often heavily implied from the start. Bartz, great, they couldn't develop him, but they gave him a scene of him almost falling off a roof as a kid to show why he's afraid of heights. Seriously, you finally do something not about his father and we get that?
The job system is nice, though, and I rather like the battle system present in III(DS)-VI. I did basically enjoy the game, but the story got in the way. Despite how much I heard about grinding, I really didn't have to. The jobs were set up nicely that it was more about having the right jobs (after the first world, anyways). As for the last few bosses, thank the Crystals for $toss.
The thing is, III(DS) is most similar to V, and they smoothed out a lot of the faults for that version. If you have the choice, III(DS) is a far better option. V goes down as one of the 3 FF's I'm more likely to rant about.
II
XII
VI
IX
IV
VII
III
XIII
I
VIII
VX
Also, the PS1Classic version is really buggy on the PSP. Not going to downgrade it for that, but it was annoying. Saving was a real pain, the game even froze on me a couple of times while trying to save.
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I also like III (the DS version), but for some reason I can't get myself to finish it. One day...
Just one piece of advice. When you get to the point of no return. Turn around, exit the dungeon, and save. Really wish they added a save point there. The final sequence of III is one of the most memorable endings to Final Fantasy games. If you've played Dissidia you somewhat know what's coming.
III, VI, and maybe VII were the three most memorable. Yuffie mildly degraded Sephiroth for me, her ultimate pretty much allowed her to single handedly take him out with ease. That was cool in its own way but made Sephiroth seem like a complete chump of a boss.