Prob not
Qilingham seems to be awakened or at least in some sort of near awakening state like G4 Luffy was(G4 also had the cloud vest).
Sommers was likely sent to replace Shamrock while he’s away. Sommers is similarly related to a gorosei and is a swordsman.
Doubt it. And anyway, these days Kaku too is awakened; hell, even a sword is.
HK are the Tobi Roppo of the government: aside from Shamrock, they serve the purpose of being the enemies of the low and mid mugi, the revs and maybe the SH grand fleet while the monster trio + Sabo + Dragon + who knows go against the Gorosei, Imu and Shamrock.
The stronger HK might be EoS Jinbe's fight; the stronger (Shamrock excluded).
In Gunko's case, Oda being Oda means woman vs woman and so Gunko is going to be Nami, Robin, Belo Betty or Koala's fight. That is the type of challenge we are talking about.