For a non-techy, the hurdles you just described are an annoyance in the way of getting a quick charge - not obvious security issues. After all, this charging station is operated by the amusement park/airport/conference/whatever... if it asks you to approve it why not?

And yes, in the past many iOS jailbreaks were shockingly simple. The website one in particular - you went to a URL and clicked a button... your phone rebooted and was jailbroken.