I'm not sure why I won the $500 two months running, but one thing I'm damned sure of is that I'm not a top 1000 writer - that is if you go by the amount of money earned. Up until the month I won that the first $500, I had been averaging about $40 to $60 a month, and I had been writing for a year and a month.
Unlike you, I am a damned good writer, acknowledged by many professionals to be so.
http://bestebookstories.blogspot.com/2012/09/flattering-words.html
My writing didn't change or didn't improve or didn't do anything. I just got lucky to write the right article at the right time, and that pushed my figures over $100 for the month.
I'm pretty sure that we weren't selected on the basis that we were good writers. I'm not sure what the criteria was.
I think it was based on the top 1000 earners, and if that is the case, then apart from a few top earners, mostly people don't earn that much.
I also don't follow the people you mention. I don't think they're writers. They're marketers.