Is it worth it to buy the original cartridges or the virtual console versions? For a not as costly and probably smoother overall experience, digital would be the way to go. Especially since the further you go back with originals, the higher the price will climb in comparison to PSN. Plus there are a few games that run a lot smoother and have way less load time... 11 is the only game I haven't played and I have no idea if I'm missing any story references in newer games.

Should i play the FF 7 Remake before I play the original on the PS1? Personal opinion, as the remake will have a redone combat system... I'd go with the original first. In the long run if you're working your way up from the first game, it'll give you a great perspective on how the series went from Turn Based to ATB and into the newer systems. Plus with the way nobody knows how dynamic the changes are going to be, if you play the original first you will be able to spot the differences or references to the original game once the remake is released.

Is FFXIV Realm Reborn a game only a big fan would understand? Yes and no. Even as a long time fan, besides the general "This is Final Fantasy, so enemies are weak to..." and "OMG, I recognize that!" along with some skills classes have or what the classes will do... You won't miss much by not being very familiar with the series.

There are nods to a few things, or references that might go unnoticed. But the game itself is completely set apart from everything before it, except maybe XI... but I'm unsure about it.

Either way, Final Fantasy to me has always been a series where friends or I got curious about it at one point. Started on many different points, and ended up going back and playing the rest of the games. You'll be fine no matter where you begin.