Obviously you are not obligated to help. It’s not a sustainable situation so I get that. But let’s not call it “tough love” either because it has nothing to do with tough love.

Anonymous wrote:I have only one brother with some mental illness and he lives with my parents. We support them financially. My parents get social security and pay for food. We paid off their house. We now own the house. We pay for all their bills.

My husband earns a lot of money. We live a very luxurious lifestyle. Even though we already help my family, I often feel guilty we do not do more.

I have some extended family and I do not help them. It stops with my brother and parents.

If I were OP, I would probably try to help out my siblings. It would of course depend on how much the HHI was and how my husband felt about it.

We paid off their house. We now own the house.

lol. What a martyr you are. How gracious of you.

Anonymous wrote:Another scenario: Two adult children, both educated and very hard working yet one is financially very successful while the other struggles to pay the basic bills because of bad luck and circumstances beyond their control. The wealthier child offers no help to the other,. Therefore, I feel compelled to occasionally step in with financial help. I am relatively comfortable but not wealthy. The relationship between the two of them is tense. Any suggestions?

My suggestion would be to be a little more flexible in your thinking. It's possible the wealthier child does not view this situation as entirely bad luck and circumstances beyond their control. You sound a little defensive about your struggling child and I find it hard to believe they have no responsibility for their problems.

If the wealthier child will likely have to step in once you run out of money or die, it's reasonable for them not to be giving any money now.

And also, they are adults now and their relationship is not yours to manage.

Another scenario: Two adult children, both educated and very hard working yet one is financially very successful while the other struggles to pay the basic bills because of bad luck and circumstances beyond their control. The wealthier child offers no help to the other,. Therefore, I feel compelled to occasionally step in with financial help. I am relatively comfortable but not wealthy. The relationship between the two of them is tense. Any suggestions?

Anonymous wrote:Brother with illness yes.

+1

Structural help for your nieces and nephews. Think about what might help them most stop the cycle and do that. I think it’s your best and most useful form of assistance.

I have only one brother with some mental illness and he lives with my parents. We support them financially. My parents get social security and pay for food. We paid off their house. We now own the house. We pay for all their bills.

My husband earns a lot of money. We live a very luxurious lifestyle. Even though we already help my family, I often feel guilty we do not do more.

I have some extended family and I do not help them. It stops with my brother and parents.

If I were OP, I would probably try to help out my siblings. It would of course depend on how much the HHI was and how my husband felt about it.

I have siblings who are struggling and it’s because of choices they made in life. I’m comparatively doing much better but I will not help them with money in any meaningful way. I should not have to be punished for their poor choices, and besides it’s enablement. They voluntarily quit good careers for silly reasons.

There is no requirement, but I think you do need to make sure you don't enable. So if a brother cannot manage his finances and you want to help I would not throw money at him directly. I might offer to pay for a class or an advisor and if he was say overwhelmed with medical bills, I might offer to pay that. If a sibling got a job, but could not afford a car and the bus ride was an hour and a half, then I would help buy a car.

My husband fell into the trap of just giving money and trusting and felt pretty used because they ended up just buying frivolous things and asking for more. They bought themselves we would not buy because we were thrifty and liked to have a big safety net and save for our kids' college.

That said, there is no obligation, but always be focused on giving a needed boost or leveling the playing field NOT on enabling dysfunction and rewarding poor habits.

Anonymous wrote:I’m one of four kids and the only one who is financially secure. I have 2 brothers who never attended college and 1 sister that struggles financially despite having a Masters degree. One brother has learning disabilities, lots of kids, and has never maintained any kind of long term employment. He lives with my parents. Older brother is married, owns a home, but has had long term health issues that have prevented him from working the past few years. His wife has been unemployed ...

In what ways would you feel obligated to help? At what point do you say no more? I’m truly torn at where our generosity ends and tough love begins.

1 Brother- LD's, lives with parents, numerous kids that I assume live with an ex spouse or partner. No support since he lives with the parents.
2 Brother- health issues, wife unemployed, has mortgage. Kids? FMV house? 12k out by OP over 2 years so that set needs cheaper housing. No $ from OP. Neither employed so they are not in a locality due to employment -move in with parents who can no longer afford to maintain 2 households and already have 1 in their house.
3-Single sister - masters degree. No $ from OP.

OP funding 4 residences is just silly so cut it down to 2 - parents + OP.

One option when your parents pass is to give up your share and split it among your other siblings. I think that gesture means a lot.

I have a brother who has never been able to hold a job for more than 2 years. He now is jobless again and has no concerns about finding a new job. He will get unemployment and has some potentially serious health issues and could easily find himself with an unexpected health event yet refuses to buy health insurance that he can afford because his state has a very good health plan for low income residents. He also maintains multiple storage units for collectables that are not worth the cost of these units. I told him that he made his bed and he has to figure it out. I managed to cobble together a reasonable savings for my eventual retirement and our surviving parent also has significant assets that support her living expenses. If he does suffer an unexpected health emergency, the first place he will go to for support is me or the “bank of mom”. We’re worried that he could impact all of our retirement because he refuses to take care of his own business.

We help my SIL as needed. It’s a pleasure to do so.