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My friend is terminally ill. Should she sell her rental home and pay $100,000 in capital gains?

A terminally ill woman faces a difficult financial decision regarding her rental property. She owns a condo that generates rental income but now requires costly care. Her younger son lives in the unit but plans to move out soon. Selling the property would trigger approximately $100,000 in capital gains taxes. The situation raises questions about asset management during end-of-life planning.

Capital gains taxes apply to the profit from selling an investment property. The IRS taxes these gains as ordinary income for the year of the sale. A $100,000 tax bill represents a significant portion of the sale proceeds. This reduces the total funds available for medical care and other expenses. Owners must weigh the immediate tax burden against long-term financial needs.

Several strategies can reduce or defer the capital gains tax liability. A Section 1031 exchange allows reinvestment in a similar property to postpone taxes. However, this requires identifying a replacement property within strict deadlines. The process adds complexity during an already stressful time. It may not suit someone focused on liquidating assets for care.

Another option involves the primary residence exclusion if the owner lived in the condo recently. The IRS permits up to $250,000 in tax-free profit for single filers. This requires living in the home for two of the past five years. Renting it out for longer periods disqualifies the exemption. The owner must verify her occupancy history to see if she qualifies.

Selling at a loss could offset the tax burden if the property value dropped. But most markets have seen significant appreciation, making a loss unlikely. A stepped-up basis at inheritance eliminates capital gains taxes for heirs. Holding the property until death transfers it tax-free to beneficiaries. This strategy benefits the son who would inherit the condo.

The son’s plan to move out complicates the rental income stream. Without a tenant, the property generates no cash flow to offset carrying costs. Empty units still require mortgage payments, insurance, and maintenance. Selling quickly avoids these ongoing expenses but triggers the tax. Timing the sale before year-end may affect the tax bracket.

Consulting a tax professional or financial advisor is essential for this decision. Individual circumstances vary widely, and tax laws change frequently. A fiduciary advisor can model different scenarios and tax outcomes. They can also address Medicaid planning and estate considerations. Professional guidance prevents costly mistakes during a vulnerable period.

For terminally ill owners, liquidating assets often takes priority over tax optimization. Access to cash for medical care and quality of life may outweigh tax savings. Selling the condo provides immediate funds for treatment and comfort. The $100,000 tax bill is painful but may be unavoidable. Peace of mind and financial security for remaining family members matter most.

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