I'm confused....

There's a couple of things I don't understand -

1. So what exactly was Hoffman's test? Jill put him in the reverse bear trap as per John's instructions but why was he tested and what was the actual test? What was he supposed to do/sacrifice in order succeed? John never puts people in unwinnable traps.

2. What happened to Bobby then? He didn't succeed on the last test, did he die too or was the purpose that he was to live knowing he got people killed because of his lie, along with his innocent wife?