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Having no income does't mean they do not have taxable income. If they keep their unearned income bellow certain limits, yes it is possible that their social security income is not taxable and they do not have any capital gains tax. If they accumulated enough wealth or most of their investments is in nontaxable investment vehicles like ROTH IRA, yes it is possible to have cash flow but no income tax. It is all about money management.
Rental income often result in very little rental profit (after deducting depreciation and other expenses). If the building is in a trust, there may not be any rental income. And the houses could have revered mortgage, which means no mortgage and nontaxable income. Having assets doesn't mean that she cannot ask or have a charitable organization pay for her medication. It is up to the donors. It is not illegal to give money to somebody with medical condition. While the government help is limited to people with little asset, private charity is not always only for the poor or helpless. As long as they do not hide money from the government and use the legal loopholes to avoid income tax there's nothing illegal about it.