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.