Record producer Damon Dash’s problems just keep getting worse. Fashion designer Rachel Roy filed for divorce from Dash, co-founder of Roc-A-Fella Records and Rocawear, last week in New York. The couple has been married for four years and has two daughters.

Dash, who in 2005 sold his stake in Rocawear to Jay-Z for $20 million, has run into substantial legal issues over the past year. Although he was previously thought to be worth about $50 million, he now apparently has lost that fortune. He reportedly owes $2 million in state taxes. A bank has started foreclosure proceedings on his two Manhattan condos.

A judge ordered Dash’s luxury Chevrolet Tahoe SUV seized last year when he couldn’t make the $714.99 monthly payment. He also faces lawsuits filed by law firms and landlords for unpaid bills.

This won’t be Dash’s first go-round in the family court. He and ex-girlfriend Linda Williams have battled regularly for years over their 17 year old son Damon, Jr., a.k.a. Boogie. Dash has sole custody of Boogie. Just last fall, Dash has to request a court to order Williams to return Boogie to his custody after a visit, even enrolling him in a school near her home.

More recently, Williams claims that Dash did not have Boogie enrolled in school and complained that he was allowing his on to pursue a career as a DJ at the expense of his schooling.

Dash’s current financial woes will make the distribution of property and determination of child support very complicated in his divorce from Roy. Division of debt, especially when it outweighs assets, is always very difficult in a divorce. Dash certainly won’t be paying the $40,000 a month in child support that fellow hip-hop mogul Russell Simmons pays – but how much will be appropriate in Dash’s circumstances? We’ll wait and see.