I’ve paid to enter some contests. I don’t mind it when I win, but it’s a double hit when I don’t.
I’ve paid from $1 to $20, and each time they gave a compelling reason why I needed to compensate them to consider my work. And each time I’ve felt duped afterward.
Going forward, the only reason I’ll pay to enter a contest is if I’ll receive feedback on my submission. So far, I’ve never seen this service offered in the contests I’ve considered.
Also, beware of bogus contests, whose only purpose is to make money for the contest owner through the submission fees they collect. Research contests carefully, and steer clear if you have concerns.