Strategic Tax Moves: Roth Conversions and New $1 Million Capital Gains Proposals
By TopHolding Editorial · Wednesday, June 17, 2026 at 9:01 PM

From Roth conversions to hiring family members, tax diversification and new legislative proposals are reshaping how Americans plan for retirement and legacy.
Aggressive tax planning is becoming a necessity for both individual retirees and small business owners looking to maximize their long-term wealth. For individuals, financial advisors are urging a serious look at Roth conversions, which allow for tax-free growth and withdrawals, a strategy that is particularly effective for those with a longer time horizon or those who expect tax rates to rise in the future.
Business owners have unique opportunities to lower their taxable income by hiring their children. If IRS rules are strictly followed, the salaries paid to children are deductible business expenses, and the children can often earn up to the standard deduction amount without paying federal income tax themselves. This not only builds a family legacy but serves as a significant income-shifting strategy.
On the legislative front, a new proposal on Capitol Hill could provide substantial relief for older homeowners. The bill proposes a $1 million capital gains tax exclusion for seniors selling their primary residences—double the current limit. This move aims to help retirees unlock equity in their homes to fund long-term care or other retirement needs without facing a massive tax bill from decades of property appreciation.