These characters are an elite group who have worked together before. It's very likely they won't make it out of the rebellion alive. There should be camaraderie between the characters. They should work together very well. There will be other npcs in the group providing backup/whatever, but these are the lead three.
It should be noted that these characters can be played as NPCs, and their actions will be played out in other threads until or if players pick them up.
Feel free to change the names.
A tentative means of them knowing each other is that Chirp's family served Remmeke's family. When Remmeke's family fell from grace he and Chirp were picked up by Paragon five-ish years ago and that's when they met Gil. Please feel free to come up with something entirely different!
Taken by James

Image credit to artastrophe.
Purpose: The tech/magic guy of Awakened. Player must have been a member for 6 months with one character approved.
Name: Gil
Gender: m
Age: 30s-40s
Character details:
- This man is highly learned. He is the chemical/alchemical expert, and has expertise in structural integrity/architecture.
- Small magical ability in relation to his expertise.
- Sharp wit.
- Grew up in the historical district.
Character ideas:
- What break got Gil out of the historical district? How did he get so book smart?
- Loves making fun of Remmeke, especially for his poetry?
- Poor hearing/awareness of the world around him? Horrible sense of time?
- Enjoys engaging in low-brow humor fests with Chirp?
- Frustrated when he is unable to explain his ideas/thoughts?
- Has a hard time staying fit enough for Remmeke's expectations? Tends to tire out easily?
- Gets laid 10x easier than Remmeke, despite being classified as less handsome?
Taken by Jason

Image credit to anndr.
Purpose: The strategist and swordsman of Awakened. Player must have been a member for 6 months with one character approved.
Name: Remmeke
Gender: m
Age: 30s
Character details:
- The unspoken leader of Awakened. The man with the plan and responsibility.
- Tries to be the most strict and serious. Has a love of bad poetry he tries and fails to keep secret.
- Master swordsman. Alternatively, master magic user of some sort.
- Able to make good decisions under pressure.
- The linchpin of the group. They look to him for guidance even as they pretend to not take him seriously.
- Elf synevive. Old gentry that has fallen on hard times, close to ruin.
Character ideas:
- Can't help laughing at Gil's jokes despite his best intentions?
- Relies heavily on Chirp's skill even while treating her like a kid?
- Great at improvising?
- Great at logic puzzles?
- Some sort of stress related addiction/illness? Ulcers? Early balding? Headaches/eye strain?
- Has a hard time sleeping/tends to obsess over little details, not giving himself enough time to sleep? Gets nagged at by Gil/Chirp?
- Tries to make the other two act more mannered, fails horribly?
Taken by Tov

Image credit to me-illuminated.
Purpose: The fighter of Awakened. Player must have been a member for 6 months with one character approved.
Name: Chirp (has not been called by her real name for years)
Gender: f
Age: late 20s-early 30s
Character details:
- Has mastered magical swordplay (how you make it work is up to you) that makes her very, very dangerous. Better at the sword then Remmeke.
- Spunky. Loves awful humor.
- Born into a family who served Remmeke's family.
Character ideas:
- Not afraid of death?
- Reckless?
- Unconsciously uses her magic through swordplay and has always done so? Was not aware of it until Gil told her? Perhaps it translates to hyper awareness and sorta an extra-sensory perception of people around her? Perhaps can latently sense magical ability but doesn't realize that's what she's sensing, instead feeling it as people she should be wary of?
- Gets on super well with Gil, feels sorta rivalry/sibling-like love/resentment for Remmeke?
- Good at following orders?
- Has a super hard time learning how to read/write/other scholarly pursuits?
- Has the most crooked/dirty mind out of the three, and is often chastised for it?