[0] http://linuxoniphone.blogspot.com/2010/04/ive-been-working-o...
edit: in 2012, it was deemed not a violation of the DMCA to jailbreak a phone. Whoops.
I don't know what the consequences of exploiting a hole in their security implementation or possibly violating their ToS or EULA.
Trying to profit from such an exploit commercially would test the waters by attracting Apple's legal department.
[0] http://linuxoniphone.blogspot.com/2010/04/ive-been-working-o...