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For the Week of November 21st, 2025
Passive Income Strategies, Law Shakeups, and the Property Tax Pushback
This week’s retirement news pulls back the curtain on a shifting landscape that could catch even the most prepared retirees off guard. From rising retirement ages and under-the-radar risks in supposedly “safe” insurance products to new tax law curveballs and growing tensions over property taxes, the rules of retirement are evolving fast. Add in a massive generational wealth gap and the challenge of aging in homes that aren't built for it, and it's clear: today's retirees need to be more strategic than ever.
By RetirementRedFlags.com
Longer work lives, tax traps, and insurer risks are reshaping what retirement really looks like.
1. Retirement Age Keeps Rising - Is Passive Income the New Strategy?
The average retirement age continues to increase as more Americans delay leaving the workforce, whether due to financial necessity or personal choice. Traditional retirement planning focused on building a large nest egg, but with rising costs and longevity, many experts suggest shifting the focus toward generating consistent passive income. This includes income from investments, rental properties, annuities, and other sources that can provide more flexibility and financial stability in later years.
Action Steps:
✔ Evaluate your long-term income streams and how they align with your retirement goals.
✔ Consider adding passive income sources to supplement traditional savings.
✔ Reassess your retirement age expectations based on income readiness, not just savings totals.
2. Hidden Credit Risks in Insurance Products Could Threaten Retirement Security
A new Bloomberg report reveals that insurance companies - long seen as safe havens for retirees - are increasingly investing in risky credit assets like structured debt. These complex investments could pose major risks if markets falter, potentially threatening the guarantees that retirees depend on from annuities and life insurance policies. While not an immediate crisis, it’s a red flag for those heavily reliant on insurance-backed retirement products.
Action Steps:
✔ Review the financial strength ratings of insurers backing your annuities or life policies.
✔ Diversify retirement income so you're not overly dependent on one insurer.
✔ Read your policy fine print to understand how guarantees are protected (or not).
3. New Tax Law Shakes Up Roth Conversion Timing
CNBC highlights how Trump’s recently passed “Big Beautiful Bill” alters the calculus for Roth IRA conversions. While tax rates will remain lower through 2028, new income thresholds, deduction changes, and Medicare-related implications make conversion timing more complex. What once seemed like a straightforward move may now carry surprise tax consequences or unintended effects on retirement benefits.
Action Steps:
✔ Consult a tax advisor to assess whether Roth conversions still make sense under the new law.
✔ Consider spreading conversions over several years to minimize tax spikes.
✔ Monitor how conversions impact other areas like Medicare premiums or Social Security taxes.
4. Baby Boomers Are Pushing Back Against Rising Property Taxes
As property values rise, so do the taxes - and many Baby Boomers are now fighting back. Despite owning more wealth (especially in home equity) than any other generation, many feel squeezed by property taxes that don’t account for fixed retirement incomes. This tension could reshape local tax policies, but in the meantime, it's affecting retirees' housing plans and cash flow.
Action Steps:
✔ Analyze how property tax increases will impact your retirement budget over the next decade.
✔ Apply for local senior exemptions or tax relief programs if available.
5. 74% of Americans Want to Age in Place - But Most Homes Aren’t Ready
A recent Yahoo survey found that nearly three-quarters of Americans want to remain in their homes as they age. However, many of those homes aren’t equipped for accessibility, safety, or long-term comfort. Without modifications, such as grab bars, stair lifts, or wider doorways, the dream of aging in place can become costly or dangerous.
Action Steps:
✔ Conduct a home safety and accessibility audit to identify needed improvements.
✔ Start budgeting now for future home modifications that support aging in place.
✔ Consider whether your current home will remain practical as your physical needs change.
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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