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No. of Recommendations: 3
If she is capable of learning, do the tough love for a while and then say something like "this is the last time we'll bail you out...mess up again and you're on your own

This does not work with people who are inherently irresponsible, self destructive, or simply incapable of modulating their behavior. You can’t tell an alcoholic, drug addict, compulsive gambler, or similar “OK, one more time, but that’s it.” It doesn’t work that way.

I don’t have the answer, but ‘tough love’ for these types is a recipe for failure. My advice would be to find a competent (and older) estate planning attorney and set up whatever legal structure would allow the principle to be disgorged over time but *not* allow the claimant to access the principal ever. I don’t know if there’s a way to keep the J.D.Wentworths away from such a honeypot, but I’d guess it’s been successfully done somewhere, somehow.
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