I'm glad you had a good time on the "mountain". Listening to him chatter away can give you some insight into what he's doing w/his life. Sounds like he doesn't have a whole lot going on. The things he's telling you are not to make you glad you aren't w/him...he's just telling you about his life at the moment. BTW, they all cry about having no money. They want you to think that they don't have any...but they spend it all on themselves, their toys and their fun. They want us to feel sorry for them...don't!
And, yes, they do tend to gloss over things and will deliberately ignore things that you mention. As long as you do not bring up the relationship, he'll continue to chatter away and be a "friend". Just remember, the description for "friend" w/the mlcer is not the same as what we are familiar with.
You've got a very good handle on your situation...continue to listen and validate. You'll be surprised at what you hear if you don't offer up advice, etc. Dig deeper for patience as you continue to move forward.
Sit quietly, the answers will reveal themselves when you least expect them to. The past is gone, the present is a gift and you need to focus on today, allow the future to reveal itself when it is ready.