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Laughter, the Best Medicine

William Housley  |  Sep 8, 2025

Laughter, the Best Medicine
We all know that laughter is the best medicine. And while Humble Dollar usually gives us wisdom about money, markets, and life, maybe it’s time to add a little humor to the mix. Let’s send Jonathan a laugh.
Now, humor is always a risk—especially across cultures. The Brits, after all, are famous for their love of irony and wordplay. But clean, clever jokes never go out of style. Here’s a start:
How many financial advisors does it take to sell an ETF?

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Smarter Giving in Retirement and the Medicare Gotcha 

William Housley  |  Sep 7, 2025

One of the biggest surprises in retirement is how the tax rules around charitable giving shift. During your working years, you might have claimed a deduction for every gift you made. But now, with the standard deduction so high—$32,300 for couples 65 and older in 2025—many retirees no longer itemize. That means the tax benefit from donations often disappears.
Still, there are strategies that can help you get more impact—for yourself and for the causes you care about.

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Helping a Sibling with Health Insurance Costs?

HavingFun2  |  Sep 7, 2025

After reading Richard Quinn’s recent post about Medicare, I thought this would be a good place to solicit thoughts.
I have a 64 year old brother who is single, has no other immediate family, and is currently on Medicare disability due to mobility issues.  He has a medicare advantage plan which has coverage for his prescriptions (Part D), vision and dental.  As he is now within 3 months of his 65th birthday, he has the opportunity to switch to original medicare without underwriting,

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The Long Game of Harbour Stories

Mark Crothers  |  Sep 7, 2025

I’m still at my vacation home, but the season is drawing to a close. The flock of summer visitors have flown back to the real world, to their bustling, busy lives. A vacation home is a funny old thing, isn’t it? A temporary nest for most, a place to perch for a week or two before the demands of reality call them back.
But there’s a small, peculiar flock of us who have decided to linger a little longer,

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Big Beautiful Bill Response

Howard Rohleder  |  Sep 6, 2025

I keep a spreadsheet that helps me estimate my current year taxes. As a result of tax changes from the Big Beautiful Bill and further tax changes resulting from the recent Ohio budget bill, I expect tax savings in 2025 in the neighborhood of $1800 on the Federal side and $300 on the State side. And, I expect further savings in 2026.
Political discussions are forbidden on the Humble Dollar site and this post is not political commentary.

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An Idea Every Week

DAN SMITH  |  Sep 6, 2025

I sold and delivered beer from a side-load truck for 30 years. A stack of beer weighed up to twice what I did. That was a physically brutal job, and although I hung up my hand-truck at age 50, I still pay a price for that career choice via osteoarthritis that won’t ever go away.
Next up was 20 years of preparing tax returns. Physically simple compared to my first occupation, though stressfully intense during the 3 month busy season. 

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Healthcare spending and premiums during a post age-65 retirement- facts and ideas.

R Quinn  |  Sep 6, 2025

About 5% of the population accounts for nearly half of total health spending, and many of these are older adults with multiple conditions.
Do seniors (65+) pay as much as perceived for health care?
Seniors pay a lot for health care, but it is not that simple. Many, perhaps most, seniors pay no more, even less, out of pocket, than many younger families. 
The bulk of spending by seniors is premiums, not the actual cost of care.

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How Much to Save to Retire?

kt2062  |  Sep 6, 2025

I came across the following Kiplinger article recently:
https://www.kiplinger.com/retirement/social-security/minimum-savings-to-retire-by-state
It postulates that you would need to save a minimum of 1.6 M to retire comfortably in California, the third most expensive state in which to retire. There are a lot of unknowns in how they calculate this, but alarmingly the median savings of people 65-74 in $200,000 the average is $609,230. On social media sites, people ask if they can retire on social security alone. I know this is preaching to the choir,

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Inventing Problems

Adam M. Grossman  |  Sep 6, 2025

“INVESTING IS SIMPLE,” observed HumbleDollar’s editor Jonathan Clements. “To be sure, you can make it ludicrously complicated.” And, indeed, Wall Street does just that.
According to a recent analysis by Bloomberg, the fund industry rolled out more than 640 new exchange-traded funds (ETFs) in the first half of this year—an average of more than three a day. There are now more ETFs in the U.S. than there are stocks (4,300 vs. 4,200).

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The Wheel Deal

Bogdan Sheremeta  |  Sep 6, 2025

THE OBBBA CREATED A NEW tax deduction for “qualified passenger vehicle loan interest” effective 2025 through 2028. 
It comes with a lot of rules and nuances, so I wanted to cover this topic a bit more in depth in case you are planning to acquire a vehicle soon.
So, what is “qualified passenger vehicle loan interest”?
It means any interest that was paid during the taxable year (e.g 2025) on a loan started after Dec.

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Pension Plan Buyout: The Exception to the Rule

Mark Crothers  |  Sep 5, 2025

I realize this is an anomaly, but my wife Suzie is in a much better financial position today because she cashed out her Defined Benefit pension for a lump sum payment.
Neither Suzie nor I understood the reasons why the offer was so generous. The financial advisor we consulted about the proposed surrender value also didn’t get the logic but strongly suggested we take the deal.
I don’t like little mysteries that defy normal thinking, so over the last while,

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Never Working a Day in My Life

Cecilia Beverly  |  Sep 5, 2025

I spent most of my early 20s not knowing what I wanted to do with my life – I lost track of how many times I changed my major! After graduating, I moved to Japan and spent a couple of years teaching English and exploring SE Asia. I knew I eventually wanted to go to graduate school, but I also knew that I didn’t want to continue in the field in which I’d (finally) majored. In a twist no one who knew me saw coming,

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Tax estimation tools on Bogleheads Wiki

William Perry  |  Sep 4, 2025

I recently came across the tax estimation tools page on the Bogleheads Wiki. I found the information and links useful and think it is likely that other HumbleDollar readers will also.
It was interesting to me to learn to that the AARP free tax calculator that I often use appears to be a licensed version of the current Dinkytown program referenced in the Wiki article with the Dinkytown version being updated more frequently and thus the Boglehead’s recommend over the licensed versions.

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What They Don’t Tell You About Retirement: Part 2 – Grandchildren Are Expensive

Mark Crothers  |  Sep 4, 2025

I know I and many others mockingly complain in a joking manner about our grandkids costing us a “fortune” when they visit—but with no malice intended, did you actually consider these costs when crafting your retirement spending plan?
I certainly never thought about this; it didn’t even cross my mind. Maybe I’m being too generous, or perhaps I’ve had a run of bad luck. In recent months, my granddaughter dropped an iPad, requiring a replacement, and my grandson accidentally let a toy car slip from his hand while spinning around,

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What They Don’t Tell You About Retirement: Part 1 – Everything Breaks

Mark Crothers  |  Sep 4, 2025

As I struggled out of the electrical retailer with an enormous box, a thought crossed my mind. I was grateful I had taken a pessimistic view of life in one particular area. The box contained a new flat-screen TV to replace our old one, which had recently given up the good fight. My pessimistic thoughts had led me to create a large emergency fund on my retirement spreadsheet specifically for replacing items that wear out.
I suspect,

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