TVs_Frank: Do not, I repeat, do not, touch FF2 (and possibly 3). There's a reason neither were localized until years later. MAJOR grindfests.
MGShogun: What he said. Pure grindfest. Better to start off with FF6.
No need to play FF series in chronology order. Each game is standalone and has separate story.
Honestly, if I'm going to recommend newbie to FF series, I'm going to give them either FF7 or FFX since they're good for beginners.
I'm actually near the end of FFIV (FFII in the US), the DS remake version, which is the original difficulty. The version that was originally localized in the US was easier from what I read, but I am enjoying it. And really, the reason I want to play them in order is to see how the series evolved. While the stories for each are separate, each game added new mechanics and increased the depth of the series.
timppu: I also did that "play all FF games through" when I bought FF7 and FF8 for PC (FF2jap, FF3jap and FF4jap with fanbased translations; I think I skipped FF: Mystic Quest, as it is a mere spin-off, right?)
I think I still enjoyed FF2jap and FF3jap quite a bit, IMHO they weren't too bad considering their age. I think those two were quite different from each other, ie. one of them concentrated on a story, while the other seemed to have no other story than "group of would-be adventurers drop into a hole on the ground, and start an adventure from there...". At least I didn't consider them to be worse than e.g. the first Final Fantasy game on NES.
When I play games, especially older ones, I try to not judge them on modern games. I am interested in how games evolved. For the FF games, my collection ranges across my DS and PS1
FFI and FFII I have on the Dawn of Soul GBA cart. (I have a DSlite with the GBA slot). I also have FFI on the Wii's VC, though I think some of the mechanics upgrades that the Dawn of Souls version adds make the game more fun.
FFIII I have as the DS remake, as I do with FFIV. I haven't really played III at all, but I am almost to the final boss in IV and I really liked IV.
FFV and FFVI I have on the FF Anthology PS1 collection. These are straight ports and translations of the SNES originals.
And then I have VII, VIII and IX for my PS1 as well.
I do have a few of the spin offs as well, namely 4 heros of light and revenant wings on my DS. I have also considered getting Mystic Quest on the VC at some point.
And I also have to say I disagree that there is no point to playing anything before VII. Many fans of the series consider FFIV and FFVI to be two of the strongest games in the series. Also, FFVI is, in my opinion, much prettier than FFVII.