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John Oliver does a complete show skewering Medicare Advantage

James McGlynn CFA RICP®  |  Oct 31, 2025

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Educational and funny
 

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A Nightmare on Destitution Street

Mark Crothers  |  Oct 31, 2025

It’s Halloween, l thought we could have a little scary story today…Booo👻
Mark stared into the glowing screen, watching the blood drain from his reflection. Twenty-three years feeding the warehouse beast, and the numbers whispered their cruel truth: $47,000. A ghost of what might have been.
The employer match had waited, an unopened door. But there were other hungers, other demons whispering of pleasures that couldn’t wait, of tomorrows that never arrived.
“Should’ve saved more,” he breathed into the frigid air,

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What does your daily schedule look like?

Carl C Trovall  |  Oct 30, 2025

While I am not too worried about arranging a maximally productive schedule in retirement, I am curious about what readers’ daily schedule looks like in retirement.
Mine so far is wake up when I wake up, sit outside with a hot cup of coffee as I run through my gratitudes, respond to emails, blog and do research for fun, eat lunch, do any household chores/projects, hike a few miles with my wife, read, eat supper, and then read/watch British mysteries on TV.  

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Coastal Retirement? Have You Considered These Costs?

Mark Crothers  |  Oct 30, 2025

I guess it’s one of those dreams, when retirement finally comes, buying a coastal property and living by the sea. It’s an appealing scenario, and a lot of people make the leap to live their best life at the coast. But if you’re thinking about it, have you considered the extra weather and environmental risks of living near the sea?
Although I don’t permanently live at the coast, I do have a vacation property within a few hundred feet of the sea.

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Valued but not Valuable

Matt Halperin  |  Oct 29, 2025

From time to time, I run across a news story that has the form of an “old master painting hanging for years in a local place, discovered to be a lost work of some great painter, worth millions.”
I have been trying ever so slowly to throw away things I no longer use.  I realize that some stuff may have actual value.  I found the photographer of polar bears playing I bought for my son’s room has become quite distinguished–the last sale was $1475 on eBay.

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Cash: The False Prophet

Mark Crothers  |  Oct 29, 2025

When I was growing up in a loving but economically stretched household, birthdays and Christmas presents were nice. But what really rang my bell was a gift of cash. These sometimes materialised when an aunt or uncle couldn’t think of anything better. As a kid those crisp notes were full of potential, self-directed treats, a true treasure.
My parents were exclusively a cash using family; if there was ever any excess it ended up in a bank savings account or credit union.

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Seniors are a frustrating lot. Here’s why…IMO

R Quinn  |  Oct 29, 2025

If there were red down arrows on Facebook I would have received so many in the last week, their system would have crashed. I have taken on the seniors who failed to plan for their retirement and now blame the system for their situation along with those who think they should not pay property taxes for schools or any taxes at all once they reach age 65 – because they paid their dues plus those
Many say without a mortgage you should not pay property taxes,

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The rules we didn’t follow

greg_j_tomamichel  |  Oct 29, 2025

Firstly, full credit to Kristine Hayes for this idea. I wish I could say that I thought of it on my own.
Kristine wrote about her buying and selling of houses that didn’t fit the accepted “rules of thumb” for personal finance. I was reflecting on my own financial path thus far, and ways in which we have strayed from the recommended path. Two in particular stick out.
All in equities
My wife and I were lucky to have good jobs straight out of university.

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How do Couples Rebalance with Multiple Accounts

Rick Connor  |  Oct 28, 2025

I’ve read  lots of articles about asset allocation, and how and when to rebalance a portfolio. One facet I that haven’t seen discussed often is how do couples execute their asset allocation and rebalancing when they both have similar accounts. My wife and I each have Vanguard accounts with Traditional IRAs, Roth IRAs, a joint brokerage account, and online joint banking accounts.
We treat all our accounts as one.  Our asset allocation has evolved over our working years,

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 I don’t know. Or care. But I will at the end of April.

Mark Crothers  |  Oct 28, 2025

I’m quite engaged with the Humble Dollar community and occasionally post articles on the forum. I’m also a keen reader of personal finance articles and books. Being a former business owner with a nearly 40-year-old degree in business and finance, I’m very interested in commentary and the goings-on in the business and finance world. But here’s the strange thing: I’m not massively engaged with my own retirement portfolio. I hardly ever think of it and rarely check its performance.

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Public Schools and Property Taxes

DAN SMITH  |  Oct 27, 2025

It is essential to support public education. Although four generations of my family are or have attended Catholic schools, I’m happy to pay my share. However, things are getting complicated in Ohio, where a progressive system topped off at 7.5% in 2004, has been reduced to 3.15% this year, and becomes a flat tax of 2.75% in 2026.
Filers of schedules C, E, F and K get a free pass on their first $250,000 of earnings.

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HumbleDollar Friend Request

DAN SMITH  |  Oct 27, 2025

I received a HumbleDollar friend request on Facebook this morning. I did not find this unusual because I sometimes share HD posts I feel may be helpful to people. Of course I accepted the friend request. 
I just received a private message from HD. The sender was offering free consultations for financial services. Jonathan’s picture was at the top of the message, as well as at the bottom, which leads you to believe that he is the author.

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Optimizer or Satisficer?

1PF  |  Oct 27, 2025

In an Oct. 27 Morningstar article “The Case for a ‘Good Enough’ Portfolio,” Christine Benz asks the question, “Are you an optimizer or a satisficer?” [satisfice = satisfy+suffice] Do you continually search for ways to improve your portfolio, or are you happy with good enough? Reasons exist for each; no criticism implied for either.
I’ve been a happy satisficer for decades. I’ve made a few tweaks, mostly to adjust to changing life circumstances.
What about you?

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A Simple Use of Wealth

Mark Crothers  |  Oct 27, 2025

I’m heading back to my vacation home today for a short break, maybe ten days or so. My grandkids and family will follow in a few days, and we’ll all be together for Halloween.
Over the last few years, my holiday neighbourhood and the local community have built something special: a two-day Halloween festival that’s snowballed into quite the event. There’s a fancy dress parade, a ghoulish disco party, and a spectacular fireworks display launched from the harbour by professional pyrotechnicians.

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Relearning to do Nothing

normr60189  |  Oct 26, 2025

It took me a few years in the work force to realize I was doing it wrong. For example, annual vacations should be a time to restore and rejuvenate. I began well enough, with vacations spent in the local library, learning photography, honing dark room skills, etc. This was stimulated by a lack of funds among other things.
I was the eldest son, and my father’s idea of enjoyment was fishing at the Chain of Lakes.

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