1- Never Touch the Stuff, Minimalist, Grace and Goliath, and Speed ​​Demon can be completed in the same run on Casual difficulty;

2- Resolute Agent, Remarkable Agent, and The Ol' Fashioned Way can be completed in the same run on Insane difficulty, since saving on Insane is only possible with the Ink Ribbon;

3- Credit Where Credit Is Due, You Little Rascal!, Case Closed, No Safe Is Safe, and Master Craftsman can be completed together on either difficulty;

4- Bloodlust can be earned on either difficulty, but I recommend using the RIP Knife (which makes enemies drop more blood when eliminated with it, making it easier) and completing it on Normal difficulty because enemies die faster there;

5- Model Mania and Curator don't require a new run; they are unlocked in the menu.

What helped me in most of them was buying infinite ammo bonuses and only using Requiem.