Most Helpful Guy
How do you know his financial situation? That it would cost him no more that 300$? Maybe it's not that simple and he's trying to negotiate an agreement, sometimes that takes time. Maybe he's trying to get things done the right way, same deal.
If you're with him for six months, you might ask him what's going on with his ex-wife and if you can help him out. Not being judgmental on his situation and not talking about what he should be doing (according to you) should make it easier for him to confide in you. If he doesn't, it's because he feels that it's none of your business. Which frankly it isn't.