[Phil987]

This is aimed more at companies signing up rather than individuals, but a company called Security Innovation has a product that kind of gamify's (sp?) hacking vulnerable websites: https://www.securityinnovation.com/training/ (the cmd+ctrl training)

They have a couple of fake websites that have a bunch of vulnerabilities of varying difficulty and you get points for exploiting them.

I am not affiliated with them, but saw a demo once and thought it was cool.