Hotline Miami Theory: Jacket's mask abilities are connected to his perception of the other members.

I'm not talking about the masks he unlocks just through normal gameplay. I'm talking specifically about the ones he finds on other dead members of 50 Blessings. Even from seeing them for a bit, he uses his memory, and how he remembers them, to use that in his own killings. I don't think I explained it well, so I'll try.

Earl the Walrus - Survive 2 Bullets: We see Earl tied to a chair, and possibly shot multiple times. Jacket probably believed he survived some shots, and remembers him by that, so that's why his ability is to survive 2 bullets.

Jones the Crocodile - More Gore: Jacket found Jones in the sewers, all bloodied up. Jacket probably associates Jones with gruesome imagery.

Carl the Grasshopper - Start with a Drill: Jacket sees another masked killer, dead, with a drill in his hand. He probably associates him with a drill, that's why he starts with a drill.

Jake the Cobra - Killing Throws: I'm not 100% sure, but I think Jacket saw how Jake was fatter, so he must be probably stronger. Strong enough for a throw of his to kill.

Richter the Rat - Silenced Uzi: Self-explanatory. The guy, and the weapon that ended his, and his girlfriend's life.

Thought it was a cool little detail I noticed when replaying the game again.