It's a common phrase among black people and people who use black slang. Example, "how are you a basement dweller who's unable to attract a mate but also bad at video games? pick a struggle." In this example it essentially means if you're gonna be a basement dweller might as well be decent at video games. Or vice versa. Idk that might be a bad example. The way this transman used it doesn't make sense the way the phrase is typically used.