They cry "poor me" quite often and yet, they are spending money on themselves all of the time. They want people to feel sorry for them, but you can't, especially when it comes to the financial situation that they have put themselves into.
I'm glad you aren't going to share a lot of your info about what you are doing w/him. It's okay to treat him as a friend, but that doesn't mean "sharing" your activities, etc. w/him. He's still curious about what you are doing, but he's really not into sharing a lot of what he's doing and yes, he's only going to tell you what he thinks you want to hear. Why? To keep you right where he left you.
I think you are very wise in allowing the lawyers doing the talking/work. I know you hate to be this way, but you've got to protect yourself, not only financially, but mentally and emotionally as well.
You are doing what you need to do to survive and continue moving forward. Keep up the good work.
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.