"I'm pretty calculating. I take stuff that I know appeals to people's bad sides and match it up with stuff that appeals to their good sides"

Kanye West is suggesting that he is a shrewd and tactical thinker. He is suggesting that he has the ability to determine what appeals to people's "bad sides" and "silver linings" and after that use this knowledge to his advantage. This could indicate that he is able to determine what individuals desire and after that utilize this to his benefit in order to get what he desires. It might likewise suggest that he has the ability to identify what individuals need and then utilize this to his benefit in order to provide them with what they need. In either case, it is clear that Kanye West is a calculating person who has the ability to recognize what interest people and then utilize this to his benefit.