The retiree was 66, single, living in Pennsylvania, and relying on a $1.1 million brokerage account to supplement her Social Security income. Her goal was straightforward: generate about $55,000 a year from the portfolio to cover the gap between her guaranteed income and the cost of remaining in her home. She followed the standard retirement playbook ... The Tax-Loss Harvest That Cost a 66-Year-Old Retiree $2,400 in Wash-Sale Penalties She Never Saw Coming