Ore no Genjitsu wa Ren’ai Game?? ka to Omottara Inochigake no Game datta - Vol. 1 Ch. 4 - Truth and Lie (1)

I’m confused on what the difficulty means, like is it how difficult it is to solve the case or does it mean sum else? And Is each one of these girls a murderer or is it any ongoing crime that they are in?
 
He just decided to spend thousands of yen just to test his theory ? What happened to being cautious about how he spends his money??
 

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