Taxing Situations
36 replies
AUTHOR: Howard Rohleder on 4/21/2025
FIRST: DAN SMITH on 4/21 | RECENT: Chris&Steve Hensley on 4/28
I WAS INSPIRED BY Rick Connor and other HumbleDollar contributors to sign up for the AARP’s volunteer-run Tax-Aide program. After completing 48 hours of training at a local college and passing the required tests, I volunteered two days a week at two different senior centers. I completed my first tax season in April.
Two clients, with whom I spent extra time, stood out. The first was a widow in her late 60s whose husband had always handled their finances.
WE RECENTLY MADE a down payment on our next home. After several months of research, we joined the waiting list for a continuing care retirement community, or CCRC.
We’re in our late 60s and only relocated to our current home four years ago. It’s in a metropolitan area two hours’ drive from our daughter and her young family. We know that perhaps 10 years or so from now, we’ll want to be closer to her,
MANY YEARS AGO, a Wall Street Journal article quoted a source as saying, and I paraphrase, “Young-old age should last as long as possible, while old-old age should last 15 minutes.” Those of us who have visited nursing homes can all relate to this.
Public health initiatives and medical breakthroughs have extended lifespans significantly over the past 100 years. In his bestselling book Outlive: The Science and Art of Longevity, Peter Attia argues that we should focus not just on lifespan,
THE HOLIDAY SEASON used to be a time when we’d write and mail more checks than usual. Some were gifts to family, while others were year-end charitable donations. But with the rise in mail theft and check washing, we’ve been on a campaign to limit the number of checks we write, plus we’ve almost eliminated the mailing of checks. Here are eight things we’ve done to reduce our exposure to check fraud:
We opened a secondary no-fee checking account and opted out of the overdraft protection.
WHAT HAPPENS WHEN you’re hit by the proverbial beer truck? Will it be easy for others to pick up the pieces—the pieces of your financial life, that is?
To my knowledge, my wife isn’t checking the delivery schedule for the Anheuser-Busch brewery here in Columbus, Ohio. Still, she’s worried about the complexities of our finances. I’ve made a concerted effort since I retired to consolidate and close financial accounts, reduce our investments holdings, and streamline where it makes sense.
WANT TO IMPROVE YOUR portfolio’s long-run performance? You could boost your stock allocation—something I wrote about last year—or cut your investment costs. But don’t overlook another key strategy: thinking carefully about which accounts you use to hold your various investments, or what financial experts call “asset location.”
My wife and I have taxable accounts, Roth IRAs, traditional IRAs and a health savings account. Earnings in each account get different tax treatment both now and in the future.
I’M OLD ENOUGH TO remember when companies rewarded employee anniversaries with lapel pins. The number of years you served determined the quality of the metal and how many jewels were embedded in the pin.
I also remember when two different hospitals where I worked moved away from this practice in the 1980s and 1990s. Human resources departments came to realize that many employees didn’t value the pins. Perhaps there had been a day when pins were something people wore,
I RECENTLY COMPLETED a course called England: From the Fall of Rome to the Norman Conquest. Before that was Books That Matter: The Federalist Papers. Okay, I’m a nerd, I’ll admit it.
Since I retired, I’ve looked for avenues to broaden and deepen my understanding of subjects that I was taught in high school and at the liberal arts college I attended. Back then, there were college courses,
MY FATHER-IN-LAW Carson was a stereotypical engineer—organized and precise. All four of his children know the motto “measure twice, cut once.” Carson applied these traits to his finances, which he managed on behalf of himself and Mary Jean, his wife. Mary Jean depended on this.
As they aged, Carson maintained his mental acuity, but he was the first of the two to deteriorate physically. Mary Jean was strong physically but slowly surrendered to Alzheimer’s.
SPRING TURNS A MAN’S fancy to… wait for it… outdoor power tools. Every April, I’d haul out the gas mower to prep it for the summer season. That meant a trip to the hardware store for oil, a spark plug and an air filter. Then I drove to the gas station for some new fuel.
For an hour, I would pretend that I understood the manly art of maintaining an internal combustion engine. I would gap and change the spark plug,
WHAT SHOULD I DO with the required minimum distributions from my rollover IRAs?
I’m age 65, which means that—under last year’s tax law—I must begin taking taxable distributions in 2030, the year I turn 73. I’ve been looking at my retirement cash flow, and it appears that my wife and I won’t need the money for our living expenses.
I’m investigating using the money to help fund my grandkids’ college education. I built a spreadsheet that maps my age against the age of each grandchild and determined the years they’re expected to attend college.
FRANK CAPPIELLO and Carter Randall were longtime panelists on the television show Wall Street Week with Louis Rukeyser. Panelists typically worked at investment firms, with their affiliations displayed on the screen. At some point, Cappiello and Randall retired. On the screen, each was simply identified as an “independent investor.” At least one regular guest, John Templeton, also achieved this listing after retiring from running the Templeton Funds.
That “independent investor” label intrigued me then and does to this day.
I JUST GOT A RAISE from Uncle Sam—and relief from one of early retirement’s biggest unknowns.
In December, when I turned age 65, I swapped my bronze-level Affordable Care Act policy for Medicare plus a Medigap policy. My wife was already on Medicare. Compared to 2020, when neither of us had Medicare coverage, our monthly cost today for health insurance is $684 lower.
My calculated risk has paid off. As a young adult, I set my sights on early retirement.
SEEING NEW PLACES is something my wife and I have enjoyed throughout our married life. Some families have a vacation home that’s their primary destination. I can see the appeal: a place to get away to, where everything is familiar and memories are made.
Others have hobbies that consume their free time. I’ve lived near the Great Lakes and know boaters who head there every weekend. Then there are the golfers. Enough said. Or the football fans who tailgate,
A FRIEND ONCE explained to me his theory of lifestyle creep—and how there’s a ratchet effect. Let’s say you move to a better neighborhood. A bigger house means larger utility bills. Property taxes will be higher, the lawns bigger and the landscaping more extensive. The neighbor’s cars are nicer, and the shopping and restaurants are more upscale.
Like a socket wrench, once the one-way ratchet of lifestyle creep clicks in, it’s nearly impossible to go back.
AS WE CELEBRATE Thanksgiving, I’m reflecting on what I’ve learned over the past year or so from HumbleDollar—both as a reader and as one of the site’s writers.
An article I wrote about claiming Social Security bounced back and forth a few times between me and HumbleDollar’s editor, Jonathan Clements. The breakthrough came when Jonathan referred me to a free online calculator built by financial blogger Mike Piper. I’d been trying to do my own calculation in Excel.
I DID IT AGAIN. I correctly identified a trend but jumped too soon.
When interest rates plummeted as the Federal Reserve reacted to COVID-19, I had a ladder of certificates of deposit. Some of these CDs are only now reaching maturity. Each step of the ladder yielded 2% to 3%. This looked good in comparison to the low rates available through most of the COVID period.
As the short-term CDs in the ladder matured,
I LEARNED IN COLLEGE economics classes that there’s a time value to money. A dollar today is worth more than the promise of a dollar a year from now. Result? If you’re going to promise me a future dollar, you have to make it worth my while by paying me some interest.
This was certainly true in 1980, when I graduated with an economics and management major. Admittedly, inflation was even higher back then.
DICK QUINN RECENTLY wrote about his $233 surgery. I wasn’t so lucky.
When marketplace health plans first became available in 2012 as a result of the Affordable Care Act, my wife and I bought coverage. After my wife signed up for Medicare in 2020, I switched to a solo policy. I’d been counting down the days until I, too, qualified for Medicare at age 65. With a $7,000 deductible on my policy, I was crossing my fingers that my health would remain good.
I RECENTLY WROTE about lifecare communities. These provide a continuum of services—independent living, assisted living, custodial care—to meet changing needs as a retiree ages. The lifecare contract guarantees that, no matter what happens to your money, there will be a place where you can receive the appropriate level of care.
That brings me to a recent innovation offered by some continuing care retirement communities. Called lifecare at home, it’s much less costly than moving into a retirement community,
MY NEW ROUTINE is walking directly from the mailbox to our recycling container to deposit most, if not all, of that day’s mail. For years, I’ve been steadily reducing the amount of mail I send and receive. After reading Jonathan Clements’s experience with check washing, I’m looking to take this even further.
I remember when mail was important. My wife talks of growing up in Cleveland where, during the Christmas season, mail actually arrived twice a day.
EVEN THOUGH I’M NOT a doctor, I’ve been around medicine all my life. My father was a general practitioner and I spent my career in hospital administration. I had administrative oversight over three emergency departments of varying sizes. Based on my experience, here are 10 recommendations that may improve your experience should you need to visit an emergency room:
1. If you use the emergency room (ER) for a non-acute medical condition, bring a book.
RONALD REAGAN SAID “the nine most terrifying words in the English language are ‘I’m from the government and I’m here to help’.” Government programs are put in place to address real concerns. But they often come with unintended consequences.
When created in 1965, Medicare addressed the real need of senior citizens who couldn’t afford health care, just as Social Security was established in 1935 to help seniors in poverty. Both have become pillars of American retirement,
I’VE USED QUICKEN since the DOS version, with my first entry made in August 1992. I’m trying to decide if I qualify as a power user. The fact is, there are so many Quicken features that I simply don’t use.
The product was first released in 1984 as a basic digital checkbook. It later moved to Windows and it’s now a subscription service. I love the ability to manage my checkbook, but over the years Quicken has added features aimed at managing my entire financial life.
WHEN I RETIRED 10 years ago, I need to replace my biweekly paycheck. Because I was retiring early, and there would be no pension or Social Security for many years, my goal was to use savings to create a synthetic paycheck.
During my final few years of work, I prepared by channeling most of my paycheck into both taxable and tax-deferred accounts. My pay was much higher than what I needed for living expenses.
WHEN PLANNING OUR early retirement, I realized that getting and paying for health insurance for my wife and me would be our biggest financial challenge.
Before 2010’s Affordable Care Act (ACA) took effect in 2014, we talked to an insurance agent who gathered our medical histories and submitted them to insurers for consideration. Despite two major surgeries, I was deemed insurable. My wife, due to a congenital condition that had never caused a problem but might,
MY IN-LAWS AND MY mother all moved into continuing care retirement communities after giving up their homes. My in-laws were not yet 70 when they moved in and my mother was age 75. They lived in two different communities about a 45-minute drive from one another.
Both communities provided excellent care, but had differing levels of service and had different ways of being paid. I’ve garnered further insights as a volunteer board member for a third continuing care retirement community (CCRC),
IN PROFESSIONAL sports, superlatives are often overdone. Even the GOAT designation—greatest of all time—is sometimes applied prematurely. But love him or hate him, Tom Brady is arguably the GOAT among NFL quarterbacks and perhaps among all NFL players. For proof, look no further than his collection of record-breaking statistics, Super Bowl rings and most valuable player awards.
Could it be that he has added another GOAT designation with his epic fail at retirement? Brady reversed his retirement announcement from the Tampa Bay Buccaneers after just 40 days.
I’VE FINALLY DECIDED when to claim my Social Security benefit. Along the way, I realized that calculating the ideal start date is easy—provided you can predict your retirement income needs (doable), your investment returns (hard), the inflation rate (hard), your future tax rate (hard), your date of death (hard) and what Congress will do in the future (impossible).
This particular financial journey began when I was preparing a recent blog post on the knotty issue of when to file.
READER COMMENTS on one of my blog posts prompted me to dig deeper into my thinking about asset allocation. A trip to the HumbleDollar archive led me to a Charley Ellis article where he emphasized that readers should incorporate Social Security, pensions and annuity payments into any analysis of their asset allocation and portfolio risk.
A guaranteed stream of income is clearly valuable. I knew this, but I had missed the obvious conclusion—that the net present value (NPV) of these income streams should be considered part of a portfolio.
DESPITE WHAT’S SHOWN on TV medical shows, cardiopulmonary resuscitation (CPR) can be a traumatic procedure that has a low likelihood of success. Even if successful in immediately restarting the heart, the fact that it was necessary doesn’t bode well for long-term survival.
Some injuries or illnesses happen so suddenly that there’s little time to consider options. But for many, old age creeps up slowly or a serious illness drags on and worsens. This is the point where it’s helpful to have not just a living will and a health care power of attorney,
IF YOU FIND YOURSELF with a loved one in hospital who can’t make medical decisions, it can be overwhelming, intimidating and emotionally charged. Decisions are needed and each family member is conflicted: What would I want? What would the patient want? What do I want for the patient? The result can be sharp family disagreements.
Death, the prospect of death or even thinking about death is so loaded with emotion that it can hinder our willingness to prepare.
TRAVELING DURING the holidays? As we drive east out of Ohio and into Pennsylvania, we know to fill the gas tank before we cross the border. According to the Tax Foundation, Pennsylvania has the third-highest gasoline tax in the country, behind California and Illinois, and about 20 cents per gallon higher than Ohio.
All states have to balance their budget. But they take very different approaches. This provides 50 experiments in taxation—and those taxes influence our behavior.
MY CAR EMAILED ME to say its tire pressure was low. Perhaps it’s more accurate to say it this way: An email from Subaru was triggered by data uploaded from my 2020 Forester, all part of the automatic safety and maintenance technology built into the vehicle. The email confirmed the dashboard light indicating the same problem.
My frugal friends and I have had friendly debates about car buying. Is it better to buy a used car and avoid the instant depreciation when you drive off the dealer’s lot?
FEAR OF MISSING OUT, or FOMO, seems to be everywhere. We suffer it when we read about our friends’ fabulous experiences on social media. We can also suffer it when investing, as we fret that our friends are making more on their investments than we are.
My own concern in recent months, however, hasn’t been FOMO, but FOLB. No, it doesn’t roll off the tongue like FOMO. It’s my own invention—and it stands for fear of losing big,
WHEN I WAS IN MY early 30s, I decided to determine “the number.” What would be enough money to allow me to retire, and what was the path to get there?
Personal computers were newly available, so I decided to work this out in Lotus 1-2-3. There was no internet to speak of. Investment companies didn’t have online calculators running Monte Carlo simulations that incorporated hundreds of possible retirement outcomes and spat out a most-likely scenario with a 95% confidence level.
EARLY LAST YEAR, just as the pandemic was starting, we were looking to buy a new home in an area where houses sold quickly—but we feared selling our existing home would be far slower. In addition, home prices in the new area were substantially higher.
We had no first mortgage on our existing house and no desire to take one out for the new home. Still, we wanted to strike quickly if we found the right place to buy,
IN MY LATE 20s, I found that I was 15 pounds heavier than when I was in high school. My cholesterol was over 200 and rising. I was huffing and puffing while mowing the lawn.
I didn’t like where this was going, plus I didn’t want to buy a new set of business suits. I decided that investing in my health was as important as investing for my wealth. If my health was shot by the time I retired,
OUR HIGH SCHOOL principal returned from a teacher recruitment fair and announced to the school board, “Tell your children or grandchildren: Do not get a degree in elementary education.” He went to the recruitment fair looking to hire some very specific specialty teachers for the high school. He mostly met new grads with credentials to teach elementary school—who were looking for jobs that simply don’t exist in our region.
Our superintendent explained that our region had several large,
THE GAMBLING TRUISM says you can’t beat the house. That brings me to a recent HumbleDollar article that discussed choosing either a Medicare Advantage plan or traditional Medicare with an accompanying Medigap policy. Almost two dozen readers weighed in with comments.
My two cents: Never forget that the managed-care companies offering Advantage plans are mostly for-profit companies that are publicly traded. The government’s purpose is to transfer its insurance risk to those companies.
ON MONDAY, OCT. 19, 1987, stocks plunged more than 20%. I was relatively new to investing—and the crash shocked me. I realize now that, when you’re starting out, no matter how much you study, the trait you’re most lacking is perspective.
When I began investing, I approached a successful investor and asked for tips to learn about the market. Part of his advice was to watch Wall Street Week with Louis Rukeyser on PBS.
I WAS SITTING AT MY computer one lunchtime when an email popped up from one of my credit card companies, saying I’d just purchased nearly $12,000 of jewelry at a store in Toronto. Within minutes, I was on the phone to the card company.
I was quickly referred to the fraud unit. I told my story. The company credited my account, cancelled the card and mailed me replacements. Weeks later, I had to complete a form,
IMAGINE YOU PLAN to retire next year. What can you do beforehand to gain the most later on? Here are some ideas to consider before you log off at work for the last time.
If you’re retiring mid-year, increase your 401(k) or 403(b) contributions. Raise your savings enough to make a full year’s allowable contribution in the months you have left. This may be your last chance to put away tax-deferred money. I retired mid-year,
I SERVED ON a scholarship committee for a local foundation. We offered awards to college students entering their sophomore year. Our coordinator had the unhappy job of explaining to some students and parents that, even though their students had a full freshman schedule and passed all their classes, they didn’t actually have sophomore standing. How can this be? The answer is remediation.
Almost 24% of entering college freshmen at Ohio universities required remediation in English or math and 6% needed both.
WANT A CONSERVATIVE strategy that can help you prepare for college costs? Consider prepaying your mortgage.
In 1992, when my oldest was 10 years old, we moved to a new home. We opted for a 15-year mortgage at 7.625% with 33% down. With our son’s graduation set for 2000, we began to prepay the mortgage so the last payment would coincide with the month before he began his freshman year. Thereafter, the payments previously sent to the mortgage company were instead directed to the college.
WE’RE PROGRAMMED to believe that a four-year college degree is the only path to success. After spending several years on both a small-town school board and an economic development board, I saw the disservice that this belief is doing to many of our students.
Students and their parents are led to believe that everyone is taking a college prep curriculum in high school. There are indeed students who are actually preparing for college.
CONGRATULATIONS, your family has grown with the arrival of a first child or grandchild. As the celebration subsides, reality sets in: You want to do everything you can to pave the way for a secure future.
For new parents, the first step is to obtain two basic documents that’ll last a lifetime: a birth certificate and Social Security card. The hospital will start the process, but you need to be diligent. Is the name spelled correctly?
LIKE MANY BABY boomers, my wife and I have watched our parents go from total independence to assisted living to death. We’ve been thankful that, at key moments, they made the difficult decisions themselves, without our prompting. These decisions included when to give up the family home in favor of moving to a continuing care retirement community, when to give up their car and driver’s license, and when to move to assisted living.
Our parents were organized and realistic people who trusted us to act for them in increasingly significant ways as they moved from one stage to the next.
Comments
Thanks, Jerry. Let's pass this along to all tax volunteers... AARP and others!
Post: Taxing Situations
Link to comment from April 22, 2025
I agree about the view you get into the lives of others who are living on very little. I am struck by the high percentage of clients who have zero interest earnings, let alone stock dividends. It says to me that they have no investments for their retirement. They may have good pension income plus social security, but apparently little else.
Post: Taxing Situations
Link to comment from April 22, 2025
Thanks for the reminder that you need to make sure you have the new IP PIN every year. Like multi-factor authentication, changing the number for each encounter is a protection.
Post: Taxing Situations
Link to comment from April 21, 2025
I have mixed feelings about what I read about the IRS Free File. It is upsetting that tax preparers and tax software providers are the main force lobbying against it when the target audience is those with lower incomes and straightforward returns. On the other hand, I wonder if it will be effective for most of our AARP clients. The people I worked with are intimidated by the process and lack comfort and understanding regarding what numbers are important and how they impact their returns. I don't think the need for free volunteer programs is going away any time soon.
Post: Taxing Situations
Link to comment from April 21, 2025
Thanks for the comparisons. I'm sure our sites were similar in their distribution. One stat you didn't mention was that very few of our clients itemized their deductions. I'm watching what Congress does with the standard deduction because the higher standard deduction indexed for inflation that was implemented in 2017 was so beneficial to our client group. I hope you recall Rick that your past articles are what inspired me to volunteer for this worthwhile program!
Post: Taxing Situations
Link to comment from April 21, 2025
I'm not positive about this... maybe someone out there knows: I believe the fund must subscribe to a use an index. In other words, it costs them money to track the S&P 500. If they use a proprietary index, they save that cost. This may help them maintain their zero fee. Thanks for the info. I'm switching my FXAIX for FNILX today.
Post: Fidelity ZERO Funds
Link to comment from February 9, 2025
Eligibility is based on complexity of the return…there are areas of taxation in which we are not trained. All ages are welcome though most clients are older.
Post: Many Unhappy Returns
Link to comment from June 19, 2024
I certainly know ethical advisors and have no intent to disparage them all. The unsophisticated investor by definition is most likely to fall prey to the others. As in many areas of life, It’s caveat emptor… let the buyer beware.
Post: Many Unhappy Returns
Link to comment from June 19, 2024
Simplifying the tax code is a worthwhile goal… one I suspect we’ll never see. We saw clients who had only just learned of the Tax Aide program who had previously paid $250 to $400 for tax preparation for simple returns. What a drain for low income people.
Post: Many Unhappy Returns
Link to comment from June 19, 2024
What a wonderful way to remember him
Post: Many Unhappy Returns
Link to comment from June 19, 2024