Question: I am 53 and have been divorced for 22 years. While we were married, at my husband’s insistence, I underwent breast augmentation and had my nose fixed. For some freaky reason, all of my incisions became infected and, after several surgical efforts to fix the problems, I was left scarred for life.

After a couple years of me being depressed, having recurring infections, and losing a malpractice case, my husband decided to trade me in for a newer model. My string of bad luck continued when, during our divorce, he lost his job along with the health insurance that had covered me. Since my doctors said I would need future treatment and possibly surgeries that would probably not be covered by health insurance, my husband, who had inherited money from his uncle, agreed to pay the cost of my non-covered medical expenses that exceeded $2,500 per year with a $10,000 maximum per year.

Because of my disfigurements, I had a hard time getting back to work. For four years after we divorced, he paid a total of $36,000. Then he went back to court (I couldn’t afford a lawyer) and the judge amended our agreement to provide that my ex didn’t have to pay my medical expenses if his taxable income was less than $30,000 in any year. He was self-employed. Since then, I asked for payments, but he refused, claiming he didn’t earn $30,000 that year. I didn’t have the money to fight him and moved away.

I finally got a job and have insurance now, but I used my inheritance from my mother to pay more than $55,000 in medical expenses. I have not remarried; he did. I understand that he went on to become very successful, but he recently died in an automobile accident. Would it be a waste of time and money to try to collect from his estate, which leaves everything to his second wife?

Answer: By tying your medical payments to a proviso that your husband’s taxable income from own business had to reach $30,000 annually, the judge put the fox in charge of the hen house. Based on what you tell us, all your husband had to do was to pay his new wife a salary or lease an automobile of sufficient cost to keep his income below $30,000 in order to avoid making payments to you. Since you didn’t appeal this order, you are probably stuck with those terms.

But you have a number of other hurdles before you could collect. If the wording of your agreement makes the payment provisions binding upon your husband’s estate, you may have a better chance than if it does not. If you do make the claim, we think you may have to go back and prove that in each year, his income reached the $30,000 threshold. If it does not, proving that he defrauded you by artificially reducing his income would be a tall order.

Lastly, because you waited so long, your claim could well be barred by what is known as "laches," that is, not asserting your claims for an unreasonable time.

If you are going to make a claim against his estate, you are time-limited based on the law of the state where his estate is being probated. While it wouldn’t be a waste of time to see a lawyer and find out your chances, we think you’re in for a long, hard fight.