No. of Recommendations: 16

I think purchasing health insurance for them is a very generous thought/offer. But, were you planning on doing it for a short time or as long as they may live? It may be very difficult to say to them, "Now that you are both in your 80's and 90's, we just can't afford to continue paying your medical insurance, especially with the new baby and the college education we have to save for. I'm sure you understand." If you choose to help them with their medical care, think carefully about what you want to offer, how long, etc.

Additionally, money spent on health insurance may not seem like money well spent to them when they are worried about losing the house. Even if they are nice people, anything you do for them may not be enough or truly appreciated if they don't really understand money and debt.

Having been through bankruptcy before, and being on the brink of it again, they didn't learn enough to change their habits and they don't understand money and debt. Here's what I'd do:

If they have access to a computer I think a subscription to the Motley Fool Boards would be the first step.

If they really want to sell the house, help them find a better (more active) real estate agent.

See to it that they go to a bankruptcy attorney and/or a CCC to thoroughly examine their options and consider restructuring debt for a repayment plan.

If it looks like they can restructure and stick to a repayment plan, then if you are in a position to, you may want to help them get caught up their mortgage but only after speaking with an attorney and having appropriate papers drawn up. They must be aware that it is not a gift; that it is a legal obligation that they must repay and that they are not home free and clear.

In sum, I would be very cautious about giving them any financial help without them first starting to understand the causes of their spending and credit habits that have gotten them to the verge of bankruptcy a second time - and seeing them start to change those habits.

Give them your support: be their cheerleader for change. But they need to work this out.

Good Luck.
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