A skeezer was the lowest level of a prostitute (if there really are any levels), and brothers got looked down on extra hard for picking them up, because most of them were on crack. Plus this was a time when everybody still thought the war was on crack, instead of on us. Anyway, meeting them on the internet instead of the streets, may have gave the image a little upgrade, because back in the day, you couldn't imagine a skeezer using a computer. They were probably able to make more money this way, because a lot men, White men in particular, were too scared to drive through the hood, and pick them up.