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Their financial security is not worth the value of your relationship with your wife and her side of the family.
My wife and I are currently helping with other siblings to support a family member who didn't save enough. I was asked my opinion about some financial things and that opinion was given and ignored, and now we are here today. I don't mind helping out at all, I think we should help provide a decent life for those in our family that raised us. That being said, I have had to make clear, that I'm not working to provide a life that my own family can't or doesn't have. At least in our case the family member carries no debt and paid off a house with their retirement money.
We have a great relationship, and this person is always very appreciative of the support we provide and now seems to be saving up small amounts of that to buy the nice things. Knowing this person's spending habits whenever they do have money, I would have hated being the one that had to try and stop them spending their own money because it was theirs and how dare I tell them to keep it invested or whatever.
If you will be completely unable to support them if they fail, this might be a good discussion to have, but it really needs to be led by their son or daughter. They should understand the math enough to have this discussion without you present. Remember, you can only give advice, they have to make the decision to budget their money appropriately. (Or go back to work again in their old age).
The worst thing you could do is make them feel stupid. When my wife and I first got married, we were taking care of debt and reading a Dave Ramsey book and her reaction to reading him was "He's telling me I'm stupid, I'm not stupid, how dare he!" We got over that in time because she isn't stupid, she just wasn't raised to save money. Even when making a table, if the evidence makes it clear they are headed towards a cliff, figure out ahead of time how to present that without it becoming personal.