If you want more ambigious characters and something which will bridge you to the Persona series definitely play Devil Survivor and Devil Survivor 2. You should find a sale for the 3DS version at something like $15 as well. The endings in that game are much more complex to achieve, and don't strictly follow the chaos/order paradigm. 

I'd also recommend playing Strange Journey. It is pretty standard SMT, but in a retro science-fiction settings.

Nocturne is great, and I'd say it does the Chaos vs. Order thing the best, so of course that is a no-brainer.

Persona 1 & 2 have interesting stories and plots (Persona 2 has the best story in the entire meta-series) but their gameplay is crap.

Persona 3 & 4 definitely take getting used to, but they are addicting. You mentioned before that you might not like their tone though.

Man Spemanig, whenever you write up something, you sure to write a lot, haha! I`m glad you enjoyed the game. It`s not my first SM game, but it`s my first mainline game (Devil Survivor was my first official one). I liked hearing your thoughts on the Law/Chaos system. I didn`t think much of it, but you make a point that they make it quite easy to point out what side your allies are on and which answers go towards Law/Chaos. I don`t like how black and white it felt sometimes. I wish choices were a little more vague as well as Walter and Jonathan. I also sort of wish there were `neutral` answers or some sort of way to get neutral. I feel like it could become more of balancing points to get the neutral path rather than going with your genuine answers. I don`t know...

I feel like more of Isabeau`s progression is in the neutral path, so unless you take that path, it feels like she`s left a little under developed. I don`t know... At least she likes manga, right?

For the most part, I really enjoyed it. The battle system and fusing monsters was fun, as well as advancing the plot. I felt I always needed to know what was happening next. It felt good playing an RPG like this again. I am hoping for more SMT in the future. I`d like to play another game from the series : )

Could you rank the Persona games? I'm wondering whether or not I should play 1 and 2, and if those two aren't better than 3, then I probably won't play them.

They are quite different games to compare. Persona 1 & 2 are traditional RPG's. Persona 2 has the best story out of any SMT game in my opinion. The gameplay is similar to the first two SMT game's gameplay. Turn-based with position mattering (within a random encounter.) The dungeons are relatively bland. However, they have better stories than Persona 3 and Person 4 in my opinon. Persona 3/Persona 4 have the life sim elements. Their combat is much better, and while the dungeons are also still pretty boring, they are not really a major part of the gameplay. 

Basically, Persona 1&2 -> Traditional JRPG's, relatively linear, good story, interesting characters, archaic and boring battle system, poor level/dungeon design, high random encounter rates, and ugly visuals. Music is great, and has a more classical feel. Enemies have a lot of personality and are interesting. Make sure you play the PSP version of Persona 1 if you can. The original PS1 version had a poor translation. Of course Persona 2 is split into two games and only one of them was localized in U.S/E.U for PS1 and the other remastered much later for PSP, so you only have one platform choice for them. 

Persona 3 & 4 -> Less serious, still good story but not as interesting, characters are more interesting for their daily personalities moreso than how they interact with the main story, combat is quicker and more fluid, no random encounters (moving enemies on screen), much better visuals and art style. Music is more modern. 

If I were to say which style did I have more fun with? Persona 3 and 4's. Still Persona 1 and 2 are decent games, especially 2. 

Perhaps I'll play 2 then. I liked Persona 3's story better than 4's, but 4 trumped 3 in almost every other way. 3 had better dungeon crawling sections, but that was in comparison. 

I'm really eyeing Nocturne, as it seems to be the closest thing to something I'd like. Aren't the Devil Survivor games SRPGs? If so, I may have a more difficult time enjoying them, even with the press turn system. I just don't gel well with SRPGs, and I'd probably need a better entry point into that genre. But I'm actually very interested in Strange Journey, mostly because it's that artist's most recent game, which is both sad, and extremely curious...

I've heard a lot of interesting things about the difference between the first two Persona games and the last. Funnily enough, P2 is quite strongly his least favorite, but it's another game that I just don't know literally anything about, other than there a girl in it with hearts on her tits. I'll look into P2 though, as it doesn't seem as... animu as the latter two.

I'll wait until after I try P5 before I decide on playing P3/4 though lol. 

I think that's what's so brilliant about Isabeau. I mean if you think about it, the MC is just as paper thin as she is. It's the first time I've actually wished that a silent protagonist would speak, but if you think about it, it's fitting. If you don't take the neutral path, you're basically seen by her as your partner's sidekick, and someone who got manipulated.

Or maybe I'm just giving them a little too much credit lol. I don't think she's great, just better than the other two in a lot of ways. I don't think the really developes much at all, but it does seem to depend on the path you take in an interesting way at least.

This is a decent review on Persona 2: EP 

View on YouTube

and Persona 2: IS

View on YouTube

If you are looking for a good entry point into SRPGs, Fire Emblem: Awakening seems to be everyone's favorite.

Since you liked SMTIV you'll like Nocturne. It is very similar, but better. I'm not a huge fan of SRPG's myself, but Devil Survivor is a lot of fun despite the SRPG elements. The core gameplay is indeed press-turn and demon merging. However, there are tactical elements and on-field turns. The fun thing about it being an SRPG is that you have three parties that you control at a time, all with their own demons, and you implement them to take out certain enemies on the field. If anything can get you into SRPGs (in prepartion for the maybe release of Fire Emblem X SMT) then I think these games will. Strange Journey is again more like a numbered title, except you aren't in Tokyo and it is a lot more science-fiction like. The characters are simplistic, but not as flat as SMTIV's, and the gameplay is more retro than Nocturne's and IV because the dungeons are first person. 

Persona and Persona 2  have a teen setting, but the tone is much more in line with the SMT series. Unlike SMT though there is a lot of grinding involved. The card system (gives you personas) is not as fun as demon merging.