Hey Deborah, it's interesting to hear how this story is continuing, thanks for posting.
After some reflection, I feel like the best thing to do would be to put him in a situation where this could come up organically. (I'm thinking... take him out to lunch with a gay friend, a psychologist friend, and an ex-Marine who's been to war and see how he interacts with them... kidding, sort of.)
The way I see it there are two different issues competing for attention here:
1. She wants to have a relationship with this guy AND she thinks certain things need to be resolved in order for that to happen.
2. She likes this guy and wants to help him/save him just as a friend who senses things are going on.
My feeling is that 1 and 2 are pretty much incompatible. All of the issues she's sensing basically would end the relationship, so it's going to be tough for them to come out in the context of sexual intimacy.
If she really finds pleasure in his company, maybe she should try not expecting anything from the relationship and taking him up on his offer of seeing other people -- not necessarily being intimate with them, but just taking some pressure off this relationship till she knows him better. He may not want to tell her anything now, but even a few months will reveal a lot if she is patient and observant.