Thank you! Absolutely incredible summary. It's a shame that the Pixel Remasters on PC don't have the QoL updates. I was hoping to play them on my Deck. Guess I'll dust off my Switch. I did finish FF13 (took me 57 hours of half focus while I watched Netflix) and I do have 13-2 on Xbox 360 but I just did not connect at all with that world or characters. Maybe if I connect with some of the other FF worlds I will go back to that one. 

That's a good question and the answer is "I don't know". I just know it's a well loved and long-standing franchise and I want to try to get off on the right foot with it so that I have more stuff to look forward to. Been feeling pretty stagnant with gaming lately even though I have a massive backlog. I just don't "feel" like playing anything so maybe a new franchise can reinvigorate that. So if FF clicks I'll be spending a lot of time with it. And if it doesn't, well I may want to try again in a few years.

I'll add that based on what I know and have seen of FF6, 7, and 9 (I know these 3 in particular are highly regarded) I like the style and vibes of 6 and 9 more. 6 is looking like the strongest candidate right now.

While there will always be different opinions, the two entries in the series that at least based on how people are vocal about it, seemed to get overwhelmingly negative impressions are the two you played. 13 and 15.
15 has since had many improvements with the release of the Royal version, such as letting you cotrol each party member, but I can't speak on its quality since I haven't played 15 aside from the demos.

And the reason I didn't play 15 yet (I'll try it at some point) is because of 13, which I did play. 
Before 13, I felt like I didn't need to watch a trailer or read a review for an upcoming mainline FF game. It would still probably be a must play for me.

After 13 my excitement for new entries, or at least the urgency to play them, has been lowered to a degree. Even if they look interesting to me.

As a side note, I think 13-2 made some notsble improvements, though the cast of characters is different/more limited.
And 13-3 fixed all my issues with 13's combat systems, at the expense of you only controlling 1 character now that takes on the role of all 3 party members by herself. And since 13-3 was basically Majora's MaskmI enjoyed the real-time npc system aspect of it. The main plot was still not particularly compelling to me, but the side stories of the inhabitants of that world made it feel more alive, like it did in Majora's Mask for me.

After those games, people seem to be rather 50/50, love it or hate it, about Final Fantasy 8. Primarily due to a game mechanic that involves stealing magic from enemies, which can be too time consuming. There are faster alternatives to this such as turning items into magic, but the game could have probably done a better job at making this clear as I believe I missed it on my first playthrough.

So, which to play first?

I think the original FF7 is a safe bet.
The Remake could be played first, but I would not do that because while in some ways it serves as a substitute for the original, in other ways it does something else, which I don't want to explain because it would be a huge spoiler. If you already read Basil's spoiler tag then you'd know, but I would rather leave that for the player to experience themselves at the intended point in the game.

Followed by 9.

I'm unsure of 6 as someone's first entry today, because some people think it hasn't aged all that well. (Although I don't know how prevalent that opinion is.) While you do have experience with 13 and 15, it's not particularly positive. So I think its best to start off with a (probabaly) guaranteed banger.

Yep, I played the PSP remakes as well and for the longest of time, I've considered them the best versions mainly due to the visual upgrade and the extra content that came with it - basically I and II on PSP is a remaster of the GBA Dawn of Souls version.

However....

1. Yes, the Pixel Remastered version imo is the definitive version of the games DESPITE the lack of the additional content (post game dungeons, extra bosses) mainly because of the remixed music, the remade visuals that are more in tune with the original game's design, the new visual effects for spells, and mainly for the QoL features it has - Quick Save/Auto Save, Encounters turn off, Exp boost up to 4x and gil boost up to 4x.

This makes playing the games again easier to stomach through (specifically for 1, 2 and 5 where it makes it less of a chore from all the encounters and grinding).

It absolutely is worth another run - infact I'm going through a new run with the Pixel Remasters right now - already finished FF1, 2, 3, 4 and currently near the end of FF5 - and will be playing FF6 , all on Switch though.

I have the QoL features on max for exp and gil - FF1 took me about 7-8 hours, FF2, 3 and 4 each took me about 10-12 hours. I'm currently 21 hours into FFV but thats because I was grinding through to make my party OP lol.

2. I finished both FF3 and FF4 remakes on DS. FF3 Pixel Remaster is the best version gameplay wise however the story is not as developed as the remake because you had unique main characters in the remake while the original 3 (which the Pixel remaster is based on) has a blank slate characters that have no background or unique characteristics , basically the same as FF1.

However what I did notice is considering I played 3 on the NES as well, there are actually character interactions in the Pixel remaster - text/conversations that didnt exist in the NES version.

Also the quick save feature helps a lot in the end game dungeon because the NES version's end game dungeon was much more difficult than the 3D remake's end game dungeon.

As for FF4 - I played through the SNES, GBA, PS1, PSP, DS and now Switch versions. For the longest of time, I've considered the PSP Remake to be the best version of FFIV however after playing the Pixel Remaster, its now my most favorite - again because of the QoL features. I personally didnt like the 3D remake as much as the GBA or PSP versions.

Either ways, 10-12 hours is what it will take to finish the two games, this is in comparison to 15-20 hours on the other versions.

Good for beginners and I still say its worth playing even if you played other versions.

3. The Pixel remaster's QoL makes the grinding easier to stomach through. 1, 2 and 5 are my least favorites of the Pixel remasters so far but the QoL features make the experience much easier than all the other versions I played. If you never beat FF5, I would go for it.

4. I havent played the FF6 Pixel remaster yet however as far as what you can get access to play (excluding emulation) - FF6 Pixel Remaster is the way to go. Just make sure you dont over level in FF6 in the beginning, start grinding (increasing the exp boost and ABP boost) only after you get Espers otherwise you wont get the level up bonuses

FF6 for GBA and FF6 mobile remake (PC, iOS/android) is my favorite (despite the visual weirdness that the mobile remakes have lol) mainly because of the extra content that came with those games. Ironically I am playing the mobile remake on Steam right now lol. So once I'm done with FF5 Pixel remaster....I'll be playing the Pixel Remaster of VI and the mobile remake of VI at the same time, kinda crazy lol.

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Basically my score on all the versions of FF1-6 I played and finished....

Final Fantasy I Dawn of Souls (GBA): 82
Final Fantasy I Anniversary (PSP): 85
Final Fantasy I (iOS): 81
Final Fantasy I Pixel Remaster (NS): 87

Final Fantasy II Dawn of Souls (GBA): 83
Final Fantasy II Anniversary (PSP): 85
Final Fantasy II Pixel Remaster (NS): 87

Final Fantasy III (NES): 80
Final Fantasy III Pixel Remaster (NS): 90
Final Fantasy III (DS): 86

Final Fantasy IV (SNES): 90
Final Fantasy IV (PS1): 89
Final Fantasy IV (GBA): 86
Final Fantasy IV (DS): 92
Final Fantasy IV (PSP): 94
Final Fantasy IV Pixel Remaster (NS): 95

Final Fantasy V (SNES): 84
Final Fantasy V (PS1): 83
Final Fantasy V Advance (GBA): 88
Final Fantasy V (PC): 91

Final Fantasy VI (SNES): 95
Final Fantasy VI (PS1): 94
Final Fantasy VI Advance (GBA): 95

The older ones are so dated in their presentation and gameplay at this point, that it's downright depressing to look at and play. So jump straight to 7,8,9 and maybe 10. That was the golden age. After those, you can transition to the 7 Remake so that enough time has passed for it not to feel too repetitive after the original, but you still have fresh enough memories so that you can appreciate the differences. The Remake is beautiful and deserving of praise in its own right. It's gorgeous, and people actually have voices now. It hits different. The second part is about to come out pretty soon. Ooh mama.

Judging by the time investment you made in other games, I'd say Final Fantasy IV would be a good starting point, it's about 20 hours long and the story is very enjoyable. It should give you a good idea of how much you enjoy the series. Starting with VI could be another option, you're looking at about 35 hours for that one.

Play Final Fantasy 5 first!

I just loved this game. Its only notable drawback to me was that its story is among the weaker ones in the series. But everything else about it was at least very good from what I remember. I liked its small but cute cast of characters, its strong sense of adventure and freedom, the overworld, the job system, its fairly challenging and fun combat, and of course the music!

I think its a criminally underrated game that isn't too far behind my top 3 overall (FF6, FF7 and FF4). If it had a better story, I would put it alongside them.

Here it is, the moment I fell in love with the game:

FFVII is a good place to start for FF. Or FF7R if you want to play an action RPG, with upto date visuals and voiceovers.

Here are the starting points I would recommend to people based on what they like.

1) FF4 - This is the ideal starting point.  If you want to really appreciate the series during it's best years, then start with 4.  However, not everyone can get into SNES games, so it is best to know thyself.  How do you feel about games like Octopath Traveler, Chrono Trigger, Super Mario RPG or other SNES style games?  If you like these games, then you will probably like Final Fantasy as a whole.  So, ideally start with 4 and they play 6, 7, 9, and 10.  If you are still hooked after that then try the other entries.

2) FF10 - This is the second best starting point depending on your tastes.  If you need graphics and voice acting that are more like a modern game, then start here.  If you like 10, then try 12 and FF10-2.  If you are still hooked after that, then you can branch out to other entries like 7 and 9.

3) FF7 (original) - This is the third best starting point.  Start here if you want to know what the fuss is all about.  I would NOT recommend you start with the Remake.  (Remake is actually made for fans of the original FF7.)  If you really like FF7, then you can try the other FF entries.  It's one of the most important video games ever made, so at least you will be able to enter into any discussion about FF7 when it pops up (and it will continue to pop up).

4) FF1 - This is the fourth best starting point.  This is ideal starting point if you really want to experience the whole series.  However, I only recommend this to people who like 80's style RPGs like Etrian Odyssey, Phantasy Star, early Dragon Quest and old school tabletop D&D (2nd edition and earlier).  If you go this route, then play the NES or NES classic version.  I don't know why, but the other versions of FF1 (like the GBA version) have subtle changes that make the game suck.  This is one reason people bad mouth this game, but also a lot of people just don't like 80's RPGs.

Honorable mention:

Final Fantasy Tactics - This is not part of the main series, but is arguably the best Final Fantasy of them all.  If you like any tactical game at all, Fire Emblem, Valkyria Chronicles, Triangle Strategy, etc..., then you must play this game.  Both gameplay and storyline are fantastic.  The PSP version is the best version, but the PS1 version is good too.

Anyway, this is where I would recommend starting based on what your tastes are.  There are other really good games in the series, 6, 9, and 12, for example, but I just wouldn't start there.  Ideally, you'd start with 4 and then play all of the good story-based games in the series.  That is really the way to become a fan of Final Fantasy.

Reporting back. I've started with FF4 Pixel Remaster on Switch. I'm really enjoying the simplicity of it so far. No crazy backstory with ridiculous nomenclature and there's still a good rhythm to the combat system and exploration. A promising start that might have me move onto FF6 but then again, I'm only about 4 hours in. Thanks for the suggestions!

This is the only one I have for the Switch. XD Now I'm curious as to why it should be avoided.