I have edited your title, in the future if you want to discuss story plot points, can you please use the word spoilers in your title or explain in the opening post that you will discuss them beforehand to allow users to avoid them if they want.
I'm sure you already made your decision but here's an answer. Marked spoiler for those who may have not played through Grand Theft Auto IV's storyline as of yet.... Secondly, for major game decisions, feel free to make double saves before doing them so you can have the opportunity to branch out and enjoy all aspects of the GTAIV storyline.
Killing DeWayne is will get you money, and well that's about it. Killing Playboy X will get you his apartment, which in it has Claude's GTA 3 outfit in the wardrobe and ultimately DeWayne will become a person you can hang out with. After his likiness for you goes up enough, you'll be able to phone him to send gang members to assist you during freeroam antics.
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