I finally found time to play the story mode and was simply wondering is there an order I should do each character's story? Also after doing Chie and Yosuke's story I still got the the "To Be...", Am I suppose to play through both their stories again?

It doesn't matter.

True endings are unlocked for every character once you finish Labrys' story chapter.

@FluxWaveZ: Once I finish Labrys' story do I play everyone's story again, like from the beginning? Also thanks for the quick reply.

@SmasheControllers: No, once you finish Labrys' story you return to the other characters and the game asks you if you want to resume from the cliffhanger or if you want to start from the beginning of the character's chapter.

@FluxWaveZ: Okay, that's good.

Also, quick note: Before you can play Labrys' story, you have to play the story of a P3 character.

I'd just like to add that you may want to avoid playing certain characters one right after the other due to the similiarities in their story paths. Namely, the progression for Yosuike, Chie, and Yukiko is very similar in terms of story beats, and so it might be better to space them out by tackling other characters in between them.

@Hailinel: That's actually the opposite to what I did...

@Hailinel: also opposite of what i did which looking back might have been the better choice but i still really enjoyed the story regardless

Basically do a p4 character and that will unlock Kanji and Teddie, do another character and you'll unlock the p3 team, do a p3 character and you'll unlock Labrys. After you beat Labrys' story you can clear everyone's story. The one's before hand are cliffhanger endings and you're able to continue from that cliffhanger or start over. Personally I did Yu, Chie, Aigis, then Labrys and then finished everyone else. :D

I did Labrys last and it was worth it. I'd recommend that. It's like all the weird interactions with the other characters slowly fall into place. It was pretty great.