Maybe. But one false step could bring it to a halt even if you were building what you felt was a genuine trust. It's all a risk. For me, it comes down to how much are you willing to take a risk to help yourself. Besides, false steps are survivable. They really are.

From everything you've written, you're in a pretty serious crisis, so trusting is doubly hard because there's so much at stake either way. Unless there's something sketchy about this guy, it doesn't seem like a bad idea to keep seeing him and building that trust, however weak it feels right now.