Vanilla Ice, the one-hit wonder rapper from the 1990s, might have faded from the limelight—but he’s quietly become a multi-hit real estate phenom. When his rapping career ended, the performer, whose real name is Robert Matthew Van Winkle, turned to buying and fixing up properties to flip. It wouldn’t have been so much of a shocker if the one-time rapper, who met with early success, had ended up a...