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For the Week of September 12th, 2025
Six-Figure Equity, Four Bills to Re-think, and the Retirement Tax Debate in Congress
A new housing survey says many in the boomer generation now expect six-figure profits when they eventually sell, even as most say they don’t plan to sell at all. Meanwhile, the third-quarter estimated-tax deadline lands Sunday, Sept. 15th, and a fresh bill in Congress aims to eliminate federal taxes on Social Security benefits starting in 2026 - if it becomes law. Here’s what matters for your retirement now.
By RetirementRedFlags.com
Big housing hopes, tax clocks, and D.C. chatter - plus the moves that actually add dollars to your plan.
1. Boomers expect big home profits, but most aren’t moving
A national poll of homeowners finds 68% of boomer owners expect $100,000+ in profit if they sold today; 61% say they never plan to sell; and 76% are tired of being blamed for the housing affordability crunch. Translation: more equity locked in place and fewer family-sized homes turning over. Why it matters: If you’re counting on a downsizing payday to fund late-retirement spending (or long-term care), timing, taxes, and liquidity all matter more than list-price dreams.
Action Steps:
✔ Put numbers to the narrative. Ask a local agent for a net proceeds estimate and timeline; price in make-ready repairs and moving costs.
✔ Stress-test “age in place.” Price roof/HVAC replacements and accessibility upgrades against your cash flow; compare to a smaller, low-maintenance option.
✔ Mind taxes. Coordinate any home sale in the same year as big IRA withdrawals to avoid bracket creep (talk to a pro).
2. Tax clock: Q3 estimated payments due Sept. 15
Kiplinger reminds retirees that investment income (capital gains, dividends, interest, crypto) typically has no automatic withholding, which is why so many get hit with an underpayment penalty. The IRS “safe harbor” rules generally require paying 100% of last year’s total tax (110% if prior-year AGI > $150,000) or 90% of this year’s to avoid penalties. One useful quirk: boosting withholding on IRA/pension checks later in the year is treated as paid evenly all year, which can help plug a shortfall.
Action Steps (By Sunday):
✔ If you owe, pay Q3 by Sept. 15 via IRS Direct Pay or your Online Account.
✔ Short on cash? Increase withholding on remaining 2025 IRA/pension payments to catch up under the even-payment rule.
✔ Set a reminder now: Q4 is due Jan. 15, 2026.
3. The “You Earned It, You Keep It Act” would end taxes on Social Security benefits
New companion bills in the House and Senate propose to repeal federal taxation of Social Security benefits (Section 86) beginning in 2026. To offset revenue, they’d apply Social Security payroll tax again on wages above $250,000 (a “donut hole” above the current cap). Sponsors say this would extend solvency to ~2058, but passage is far from certain.
Earlier this summer, the major GOP tax law did not repeal Social Security benefit taxes; instead it added a $6,000 “senior bonus” deduction for those 65+, which offers modest relief to some filers. Don’t change withholding based on headlines - nothing has changed for 2025 returns.
Action Steps:
✔ Plan under current law for 2025-2026; treat repeal as a bonus if it happens.
✔ If you pay tax on benefits now, model Roth conversions and Qualified Charitable Distributions to manage AGI and Medicare IRMAA.
4. What’s keeping retirees up at night in 2025
A new rundown of retiree worries highlights: inflation eroding savings (92%), health-care costs (86%), market downturn risk (80%), drawdown confusion (71%), and outliving assets (70%). Only 40% feel they’ve saved enough, and 62% don’t know how long their savings will last.
Action Steps:
✔ Inflation defense: Review your mix of cash, short-term bonds, and inflation-sensitive assets; trim idle cash above your true emergency fund.
✔ Sequence risk: Keep 1–2 years of planned withdrawals in cash/near-cash to ride out market dips.
✔ Drawdown clarity: Pick a rule (guardrails, RMD-plus, or bucket) and stick to scheduled “paydays.”
5. Four bills many middle-class retirees wish they’d cut sooner
If your budget feels squeezed, these four routine bills are likely the culprits. A new piece calls out credit-card interest (avg. 22.78%), mortgages carried into retirement (10.5M 65+ borrowers), costly car loans (avg. $745 new / $521 used monthly), and even lingering student loans (boomers averaging ~$43,554). These debts squeeze fixed incomes and can even garnish Social Security if unpaid.
Action Steps:
✔ Credit cards: Consolidate to a lower-rate personal loan or 0% promo and automate payoff by 12–18 months.
✔ Mortgage: Price a downsizing swap or targeted principal paydown to retire the loan before RMDs ramp up.
✔ Car: Drive the car you need, not the one you financed. Sell/refinance to drop the payment.
If you have any questions about the headlines that hit the news this week, we are answering questions in our free Facebook group The Retirement Red Flags Community. Click below and we will make sure you get added.
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