Him not being in trouble doesn't mean much to me. I didn't get caught until my late 20's...I was all over the place before then, not violence, but drugs.
Who responds to an add for a hitman unless there is something mentally off? I have my doubts since I know some of his friends, some are drug dealers... so I know they are either still in the scene, or in the case of a few, recently got clean.

Also, she wasn't rolling in cash. He just thought it would be for shits and giggles? I'm unable to quite buy that whole story, but you never know I suppose.