Spousal Support Not Payment questions

[kennys2003]

What is the name of your state (only U.S. law)? Illinois / Florida

Sorry for the length of the post, but I appreciate any advice given.

I'm doing some leg work for a situation we have. My mother and stepdad got divorced over 2 years ago, and agreed to spousal support for 50k a year for 7 years.

We are in year 3 and he's stopped paying. He owes at least 30k for this year. She's 56 and is having trouble finding work (she was a homemaker the 25 years of their marraige raising their 4 kids). She is coming to us now needing financial assistance, so we are trying to figure out what our options are.

He says his financial situation is bad, he is self employed, owning 2 businesses, one which is a real estate company that rents and flips houses. This is touchy because 2 of the siblings involved work for him, the other 4 of us do not.

Obviously we could get a lawyer to enforce the court order, which may or may not happen based on his ability to pay. There's no employer to garnish wages, could lien's be placed on the assets or somehow divert the rental income to her instead of him?

My questions are:
1. What would be a good guess at lawyer fees including retainer for a lawyer in Illinois? She currently lives in FL, so I don't know how this effects the issue.
2. Is there any way to come up with a binding contract where the family pays his support and he's required to pay us back?
3. Are there any other methods or advice to approach this situation?
4. What hoops would the lawyer have to go through and what are the likely outcomes?

Thank you again for your help
Ken