Stop the emotional roller coaster (at least where he is concerned).
First, enforce the court order. If he don't pay, he don't play (check laws).
Second, Enforce the court order. If he needs money for his visit, events, ect.. unless ordered, let him ask someone else (tough I know, kid may remeber the visit, but they won't remeber you paying for it).
Third, Enforce the order, unless so ordered, she doesn't have to be the supervisor, make him pony up the cost of a "court" supervisor (they won't take the "I can't afford it" excuse for very long). You may even get the court to hire you but I wouldn't. I know many would argue but its not about the kid, it about you the parent. Sometimes you have to take a tough stance. Letting someone use a child to take advantage of you is just stupid.
Last ENFORCE the court order, do not give an inch, be nice, or do any one time favors (just adds fuel to the "taking advantage of" fire).
Been there done that, No support, All kinds of empty promises, No delivery, Kids begging to come home, etc... Stop being a patsy and make this guy pony up. I know its hard but I guaranty if you don't, he will continue to whine and take advantage of the situatuion.
Thats for Her, For you;
Layout where you stand and leave it there. When my wife comes at me over an issue with one of her kids she is told EXACTLY what I think, not what she wants to hear. If she chooses to do something else she knows there will be no sympathy form me when it blows up in her face. I expect no less from her.
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