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For the Week of October 31st, 2025
Orlando Ranks #1, Maximum Taxable Earnings Rise, and Millennials Sharing Smart Money Moves
This Halloween week, the real frights aren’t ghosts and goblins - they’re inflation, housing costs, and the ever-changing rules of retirement. But there’s good news: from Orlando’s sunny reign as the top U.S. retirement city to creative new ways retirees are finding community (and even heading back to campus), the headlines are full of financial treats too. Here’s what’s worth knowing and how to make the most of each development before year-end.
By RetirementRedFlags.com
Whether it’s finding community, managing costs, or mastering new habits, the goal remains the same: live well and plan smart.
1. Orlando Tops List of Best U.S. Cities to Retire
Travel + Leisure named Orlando, Florida the #1 best city to retire in America for 2025, citing no state income tax, affordable housing, top-rated healthcare, and year-round recreation. The broader list emphasizes that choosing where you live in retirement can have as much financial impact as how much you’ve saved. Warm-weather states like Florida, Arizona, and North Carolina continue to dominate for cost and lifestyle balance.
Action Steps:
✔ Research Orlando’s cost of living, property taxes, and healthcare facilities compared to your current location.
✔ Plan a visit during the off-season to experience the community firsthand.
✔ Factor in relocation and insurance costs before deciding whether a move makes sense financially.
2. Social Security 2026: Maximum Taxable Earnings Rise
The Social Security Administration announced a 2.8% cost-of-living adjustment (COLA) for 2026 - adding about $56 per month for the average recipient. The maximum taxable earnings will rise to $184,500, so higher earners will pay more into the system. While the increase offers some relief, experts note it still lags behind true inflation in housing, healthcare, and daily living costs.
Action Steps:
✔ Log into your SSA account to see your updated benefit for 2026.
✔ Reassess your monthly budget for inflation in healthcare and groceries.
✔ If you’re still working, plan for slightly higher payroll taxes next year.
3. University Retirement Communities: A New Kind of Campus Life
Investopedia reports that more retirees are moving into university-based retirement communities (URCs) - living arrangements that offer lifelong learning, intergenerational connection, and access to campus resources. These communities provide lectures, athletic facilities, and cultural events, but often come with steep entry fees and monthly charges, sometimes exceeding $1 million. For those who crave stimulation and community over isolation, URCs present an intriguing (if pricey) alternative.
Action Steps:
✔ Explore URCs near universities you admire and request full cost breakdowns.
✔ Tour at least one to experience the lifestyle and community culture.
✔ Compare the total long-term cost with staying in your home or joining a 55+ community.
4. Four Money Habits Millennials Have That Boomers Should Copy
Yahoo Lifestyle highlights four money habits worth adopting from Millennials: renting for flexibility, cutting unnecessary expenses, not relying solely on pensions or Social Security, and being transparent about finances. These modern habits help navigate an unpredictable economy and can serve retirees seeking to preserve wealth while maintaining freedom.
Action Steps:
✔ Reassess your housing strategy - downsizing or renting might add flexibility.
✔ Audit monthly expenses and eliminate low-value spending.
✔ Be open with family about financial goals and expectations to avoid surprises later.
5. How Much Retirees Have Invested by Age 67
According to Yahoo Finance, the average retiree age 67 has about $609,000 saved, though financial experts often recommend closer to 10 times your final annual salary to maintain your lifestyle. Many retirees fall short of that benchmark, underscoring the need for smart withdrawal strategies, delayed claiming decisions, or lifestyle adjustments to make savings last through longer retirements.
Action Steps:
✔ Review your total savings and compare it to your income goal or the “10× salary” guideline.
✔ Estimate your annual retirement expenses to see if your savings and Social Security can realistically cover them.
✔ Revisit your withdrawal strategy to balance safety, income, and growth potential for the years ahead.
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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