These goals are not sufficiently specific to be relied upon. How much more money? How dedicated will he be to school?

I wonder if he would agree to marry in a certain period of time.

What are his other conditions besides son moving in (which sounds like an unusual condition, I agree with Christina), making more money, and finishing school?

And that word conditions: It troubles me. I wonder what is really holding him back.

Are you saying that he had to pay $100,000 as part of the divorce settlement?

Are you a co-owner of the house?