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My brother is self-employed, but only makes around $20K/year. That isn't enough to pay his $24K/year health insurance, much less take care of a 4-person family.

He has survived by keeping all our co-owned rental property proceeds and by selling our late father's stocks (my brother is the executor but has not processed the estate even though it's been 7 years) and using our father's credit cards.

He periodically asks me for money; I've begun to dread the end of each month.

We co-own two rental properties. He handles the rent, maintenance, and utilities, because until a few years ago I lived hundreds of miles away.

He's never given me any of the profits. I ask. He either says "I don't have the money, I have bills to pay, I can't afford to lose my health insurance" - he has cancer - or he cites bad tenants from a few years ago that resulted in a net loss that year. I don't know what the recent profits are (or aren't) because I only get to see my purported income every 5 years or so when my brother files taxes. I can then file taxes. This late filing of taxes has cost me a lot in penalties to the IRS.

I and his friends have tried to get him to shut down the business and go work for someone. He says nobody will hire someone with cancer.

He's now at the point where he comes to me at the end of each year asking for $10K for property taxes so that we don't lose the properties.

I was wondering if there was some way to convince him that he needs to get a good paying job and start to pay me back rather than taking my money. I'm at the point where I'm living off my retirement account.

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    If you co-own the properties, your name is also on the deed, you have more pressing legal issues to resolve which will frame the relationship with your brother. Your best option is to talk to a lawyer to sort out your options, them ask how to approach you brother about them. – Johns-305 Feb 5 at 17:50
  • A partition sale of the co-owned properties (which you can force as co-owner) would seem to be in order. That would eliminate one of the points of friction. – Jon Custer Feb 6 at 20:43
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One suggestion for your brother might be setting some boundaries for what you are able to afford to do to help him. Perhaps an approach would be to sit him down, calmly and carefully, and explain your own situation. That you are currently having to live off of your retirement because of the situation you're both in - without placing blame if you can - to keep him from getting defensive and shutting down. And then, in whatever way you choose, either give him a plan outright or have him "help" you create a plan if he is capable, of how you are both going to climb out of this mess.

For Example, one plan could be: Brother, I am unable to afford these expenses any longer without seeing a return. It would really help both of us if I could begin managing the finances here, because my tax penalties are an avoidable burden. You can maintain control and will be paid a salary, etc. This way you can act as "accountant" and he can still maintain his living somewhat. The important thing would be a scenario where you are at least able to save what you need to pay the bills the business is costing you.

I don't have the ability to comment, so I can't ask any further questions, but it doesn't sound from your dialogue like you want anything more than some relief. Therefore, perhaps creating an actual partnership will work better with your brother than, say, threatening to withhold funds or threatening legal action. It is hard to infer, but seems like you don't want to create conflict, rather find a way to get him to work with you. If you can build trust he may let you help him create a budget, which would also benefit you with more peace of mind at the end of each month.

Legal action is, of course, an option, especially given the age of the estate, so getting some legal advice ahead of time may be prudent as well. However, I know from personal experience that family members and finances do not mix, so approaching this as carefully as possible first might yield more fruit than a more straightforward approach.

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