Final Fantasy X would be a good start. It's fairly easy and straightforward.

Actually, Final Fantasy XII, was one of the biggest Final Fantasy games, when talk about secret Foes, Huntings, the term "Hunter" define what you are in Final Fantasy XII, and the battle system was nice, everyone  was able to be anything from the start, the Licensing system was very nice, you could have 6 Black mages if  was you wish, and from the Start.

Final Fantasy XII, had a poor protagonist, but a good Side-characters, like Balthier, Bash, Fran, and Ashe, but the main protagonist that are Vaan, and Penelo, are not good characters, this does not make Final Fantasy Xii, a bad game, because the Support-characters, or the Side-characters, are so much alive, that fit the Hole that the Main protagonist make on the Plot. but as i said before, the Hunting, on Final Fantasy Xii, makes the game very funny, and make it worth despite having poor main characters.

other Final Fantasy games, are locked until the final of the game, or until you get on a advanced part of the game, because of that Final Fantasy VII, also is a great game, because also gives you freedom to chose your class.

Final Fantasy Xiii, was a decent game, but not the best of the Final Fantasy games, was too Linear, but instead of Final Fantasy X, had some good characters like Lightining, and some poor characters like Hope, while Final Fantasy X, all the Characters are unique, and we need each one in the plot, even when Kimahri, only speaking 130 words the entire 7 Hours of Final Fantasy X's Cut-scenes, he is a necessary, and a very good character, fits very well on the Plot.

the Final Fantasy Xiii Sequels,  the FFXIII-2, and FFXIII-Lightining Returns, are better than the Main Final Fantasy Xiii, because those 2 games were made with the help of the Creators of the Star Ocean's Series, so have  a better Battle System.

Final Fantasy IV
Final Fantasy VII (pc version +mods)
Final Fantasy X

I would start with the Final Fantasy X / X2 HD Remaster.
After that you can continue with Final Fantasy Type 0.

I wouldn't buy the Final Fantasy VII port on PS4 since the Remake will release probably later this year.

Unfortunately, this is a fairly unrealistic endeavor. Particularly the early releases are just too difficult to find (unless I want to play the iOS ports which I assume are garbage). Or I could spend like $90 to buy FFI & FFII on GBA. I'm just not willing to put in that sort of investment. Also, in order to play like, XI & XII, I'd have to buy a PS2. For XIII I'd have to buy a PS3. It's just not worth it.

I didn't know money was an issue. If that's the case, personally, I'd still buy the first game and then wait to move on when I have the money. But, it was just advice. Do whatever you want.

It's not that money is an issue....

Of course I could if I wanted to, but I just think it's crazy to go back and buy like 2 consoles (at least) and also close to $100 for 20+ year old games. 

Start with FFVII PS4 version, Then FFVII Remake later when it's out.

Yup. I've just started FFVII on PS4. About a couple hours in and I think it's pretty cool. The graphics are fine IMO, although one thing that is kinda weird is how it seems like the character models don't really belong in those environments. Never played a game like that before lol.

Indeed, FF 7 Remake, mighty release on 2017, they will not Release Final Fantasy XV, just 2-3 Months before Final Fantasy 7 Remake, would hurt the sales.