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, like accounting, that I felt I had to take to earn a living. Still, some of my favorite courses were American history, Shakespeare, philosophy and poetry. If I could go back, I might take more of these latter topics—and less accounting. But wait, I can go back. For years, retirees interested in learning needed to find a way to take a class at a local college or build their own curriculum with books they borrowed from the library or bought. Later, books on tape and CDs offered a way to bring courses to your dashboard or den. Now, quality courses can be streamed. While some educational resources are available on a subscription basis, many courses are available free or at a low cost. And those accounting courses taught me that free is good. My go-to source for serious college content is The Great Courses offered by The Teaching Company. I’ve worked my way through dozens of its courses. The company offers a wide variety of subjects. Some I have no interest in, but many others are on my wish list. The marketing material brags that the company seeks out professors known for their teaching ability. No disagreement here. I’ve yet to come across a dud. The courses I’ve taken range in length from six to 36 lectures, each 30 minutes long. The longest I’ve seen in the catalog is a 48-lecture course on western civilization. My favorites often derive from the quality of the instructor as much as the course subject. These have included: How to Read and Understand Shakespeare: 24 lectures by Prof. Marc Conner of Skidmore College. I wish I had access to this when I took my college Shakespeare class. Myths, Lies and Half-Truths of Language Usage: 24 lectures by Prof. John McWhorter of Columbia University. This changed my view of how to think about “proper” English and the uniqueness of the English language. If you want a preview, listen to the Freakonomics podcast on “Leaving Black People in the Lurch,” which is where I first heard McWhorter. Before 1776: Life in The American Colonies: 36 lectures by Prof. Robert J. Allison of Suffolk University. You learn the distinct history behind the founding of each colony and see how those experiences shaped the new country. Fun fact: You could consider South Carolina a colony of Barbados as much as a colony of England. The Secrets of Great Mystery and Suspense Fiction: 36 lectures by Prof. David Schmid of the University of Buffalo. I’ve read lots of detective fiction, including all the Sherlock Holmes stories. This course gave me new authors to explore, as well as the background of favorite writers such as Raymond Chandler and Dashiell Hammett. Schmid also weighs in on the case for Edgar Allan Poe being the first to write a detective story. Your taste will likely differ from mine. No worries. There’s content that’ll address any interest. I’ve never sought out “how to” courses, but you can learn photography, cooking, gardening and even investing. Art appreciation, music appreciation, philosophy, and many areas of science and math are represented. [xyz-ihs snippet="Mobile-Subscribe"] Courses are offered on DVDs, CDs or streaming, each with a different price point. If you go to The Great Courses website, you’ll see some eye-popping list prices for its courses. I’ve never paid anything near those list prices. The site is constantly running sales, offering coupon codes or otherwise discounting its courses on a rotating basis. In many cases, I’ve paid nothing at all by accessing courses through my local library. There are at least three ways this can be done: Borrow the DVDs or CDs from the library. Stream the content through either Hoopla or Kanopy, assuming your library offers these online resources. Pick up courses at the library’s used book sale. Yes, this costs something, but it’s often not much. Best of all, there are no tests with The Great Courses, and you can choose whether to do the homework. I took a course on The Illiad and read each set of chapters before the lecture that discussed them. No question it added to my appreciation, but no one was checking. Still, with most of the courses, I simply watch and enjoy. Howard Rohleder, a former chief executive of a community hospital, retired early after more than 30 years in hospital administration. In retirement, he enjoys serving on several nonprofit boards, exploring walking paths with his wife Susan, and visiting their six grandchildren. A little-known fact: In May 1994, Howard was featured—along with five others—on the cover of Kiplinger’s Personal Finance for an article titled “Secrets of My Investment Success.” Check out his previous articles. [xyz-ihs snippet="Donate"]

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. These managed-care companies must then manage that risk through rationing, limiting choice and negotiating provider payments, as well as encouraging healthy behavior among their customers. To the extent they’re allowed, they deny coverage or charge higher rates to those with preexisting conditions. Although Medicare Advantage was first offered in the late 1990s, enrollment really took off about 10 years ago. That was when Congress made the program more palatable to insurance companies. Advantage plans became their growth driver and industry marketing got more aggressive. Enrollment has doubled over the past decade. I looked at the major national managed-care companies in the Medicare Advantage market over that time period. Here are their stock returns for the past 10 years, without dividends reinvested, as of Oct. 18: Aetna (AET) +499% Anthem (ANTM) +537% Humana (HUM) +514% UnitedHealth Group (UNH) +873% S&P 500 (SPX) +271% Over the long haul, the stock market recognizes value. Don’t imagine that managed-care companies are charitable ventures. This factors into how they “manage” your care. Rather than choosing one of their Advantage plans, your best bet might be to become a stockholder. That way, you can smile at your brokerage statement because you’ll be betting with the house. I spent years in hospital administration sitting across the table from insurance companies. When it came time to decide, I opted for traditional Medicare plus a Medigap policy. It may cost more. But choice is a valuable commodity—and you see its true value at the most critical times in your life.

As an AARP volunteer Tax Aide for a second tax season, I completed about 100 returns and reviewed many others prepared by other volunteers. I volunteer two days a week from February 1 to April 14 at two different senior centers and continue to make observations based my clients’ tax situations. The Tax Aide program is free and not limited to seniors or AARP members. Even though most clients are retired seniors, we can serve all ages and incomes. Only more complex returns are out of scope. It is not unusual to be helping someone whose spouse has recently passed away. I had a couple of situations where the death was in 2023 which had allowed them to continue to file “married filing jointly” last year. As I prepared the 2024 return, they were hit with the implications of now filing “single.” Their standard deduction is essentially cut in half. If their income and withholding stayed the same, this meant a big tax bill. This led to difficult conversations where I explained that: 1) they had to come up with the money to pay this year’s taxes; 2) they were potentially on the hook for penalties associated with under withholding because they owed more than $1000; and 3) they had to consider increasing withholding for the current year to avoid a penalty next year. As many of our clients have low incomes, these prospects were daunting. If I saw someone where the spouse died in 2024, I was able to counsel them to increase their withholding now so they did not get caught short next year. I saw a smattering of W-2G forms. These represent gambling winnings, usually from one of our local casinos. Not surprisingly, the state and city have taken their cut and this is disclosed on the W-2G. A friendly single man nearing retirement brought in a W-2G showing about $1,600 in slot machine winnings. I congratulated him on his luck. I did the return and then the reviewer and I got to talking to him about whether he had any offsetting losses. In the end, he made a quick trip to the casino and obtained a report for the year based on his membership card. His losses for the year from playing the slots were $15,000. He had no idea. I was thinking about his situation as I was driving home that day. I would never do what he is doing… I have actually never been inside a casino. On the other hand, he was single. He had a well-paid government job for which he had a significant portion of his pay directed to his pension plan. Gambling presumably represented his preferred entertainment. If he went to the casino to play the slots a couple of times a week, who am I to say that was wrong? In the end, we could not deduct the losses… and he had to pay taxes on the $1,600. After seeing the whole picture, I was less inclined to think he was lucky. One lady came to me who had not used our service before. She had been widowed a few years ago and was anxious about sharing her information with a stranger because she and her late husband had used the same small local accounting firm to do their taxes for the last 40 years. She knew them and trusted them. She handed me last year’s return in a nicely bound booklet and pointed out the reason she came to us: the invoice tucked in the back was $360. A friend at church sent her to us. It was one of the simplest returns I did all year since all she had was social security, a pension and a few dollars in bank interest. She went away happy because she would keep this year’s refund instead of paying most of it to the accountant. We have a fair number of clients who owe zero tax on either their federal or state return. Some tell me that a friend told them that they don’t need to file anymore. While technically correct, we are taught to counsel them that filing prevents someone appropriating their social security number and filing to scam the system. More so this year than last, I am seeing clients come in with IP PIN numbers. These are six-digit numbers provided annually by the IRS to tax payers who request this identity protection. Think of it as similar to the multi-factor authentication numbers online accounts text to you. The only difference is that for victims of tax identity fraud, these are mailed to the taxpayer near the end of the calendar year. Note that these numbers are different from the PIN you are asked to put in if you e-file. One morning two out of the first three clients had IP PINs because their social security number had been compromised with a fraudulent tax filing. One man in his mid-eighties told me that his daughter had to spend hours on the phone with the IRS straightening out the fraud. He said he would never have been able to work through it without her. You don’t have to wait until your identity is stolen to get an IP PIN. The only catch is that if you proactively apply, they don’t mail you the IP PIN… you have to sign on to your IRS account each year to get it. I’ve decided to apply for one for myself…preemptively protecting my identity. I readily repeat my observation from last year: this is challenging and sometimes frustrating work. It is also interesting and rewarding. Assuming each of my clients would have paid $360 to have a paid preparer do their taxes, I put $36,000 in the pockets of people who need it for their daily expenses. Multiply that by 28,000 tax aide volunteers across the country. Not bad.

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. I did experiment with tracking some basic investment accounts, only to revert to my own homemade spreadsheets. In the beginning, all entries had to be typed by hand. This required diligence but, for me, the payoff was the ability to manipulate the data once it was entered. For a while, I used the one-click update feature, where Quicken would initiate an automatic download of transactions from all my bank accounts at once. Various glitches led me to give up on that. Now, I enter my checkbook entries manually and download my credit card transactions from the card websites, rather than initiating the transfer within Quicken. When the subscription service was added in an effort to increase Quicken’s revenues, I thought I might use the web feature to access my checkbook, rather than relying solely on the installed software on my desktop. It worked for a while. But when I had problems with the web version, I didn’t see enough value to call the help desk to try to fix it. They have a mobile app, but I haven’t tried it. I’ve never tried the budgeting feature, either. I don’t budget, so it had no value to me. Likewise with bill pay. During the years I’ve used Quicken, I’ve migrated from snail-mailing checks to bill pay through my bank. Today, I have a combination of automatic deductions and payments made online through vendor websites. With the online glitches I’ve experienced with other Quicken services, I never wanted to invest the time to test its bill pay system. Quicken offers a version that helps with managing rental properties and a home-based business. I don’t have either of those. They offer several service levels: starter, deluxe, premier, and home and office. I use the starter version. That’s all I need. If I don’t use most of their product features, how could I consider myself a power user? The answer lies in how I use the core checkbook feature. I manage four bank accounts and five credit card accounts in Quicken. When our parents were alive and we paid their bills, Quicken allowed us to track their spending and account for where all the money went. Through the report feature, I can readily track income and expenses, pull data for our tax return, compare different time periods, and run special reports on specific spending categories. The beauty is that it draws data from all accounts into a single report. Medical expenses paid with a credit card are merged with those paid from our checkbook. Once built, reports can be saved so that they can be rerun or updated. They can be viewed on the computer screen, with the ability to double click a line item and get the details behind it. Alternatively, reports can be printed or downloaded into a spreadsheet for further manipulation. Over the years, data entry has become easier, thanks to these product improvements: Autocomplete suggests entries after typing the first few letters of a word. Recurring transactions can be memorized for quick entry. Money transferred from one account to another is only entered once. Cryptic descriptions downloaded from credit card accounts can be automatically renamed to something recognizable. I still believe in balancing my checkbook. This is accomplished quickly in Quicken, compared to doing it by hand, plus this exercise catches entry errors and missed transactions. The key to Quicken’s usefulness lies in setting up the account right. Some forethought must be given to what you want to track. Set these up as categories. Quicken comes pre-loaded with numerous categories, but for the most part I’ve created my own. [xyz-ihs snippet="Mobile-Subscribe"] Once categories are set up, each entry must be assigned to a category to make future reporting useful. Subcategories are available, too. In the insurance category, for instance, you can have subcategories for home, auto and life policies. New categories are easy to add when new expenses arise. I’ve used them to track the costs of home remodeling projects and our daughter’s wedding. When these events were over, I could easily summarize the totals. When we moved, I ran a report on home improvements to update the cost basis of the house we sold. At tax time, I rerun saved reports for medical expenses, taxes paid, 529 contributions, charitable contributions and miscellaneous income for the latest tax year. Yes, it took time to enter all that data, but the payoff comes in how quickly I’m ready to prepare my taxes. I’m also less likely to overlook something. Anticipating early retirement, when I would have no regular source of income, I ran reports on my annual expenses. I downloaded these reports into Excel and made assumptions about which expenses would increase or decrease. Now that I’m retired, I run an annual report to monitor my spending. I don’t have to guess or dig to find past expenses. What did we spend on lawn service last year? What was the cost of that appliance we bought? The answer is all in one place—and at my fingertips. I think all that makes me a Quicken power user. Howard Rohleder, a former chief executive of a community hospital, retired early after more than 30 years in hospital administration. In retirement, he enjoys serving on several nonprofit boards, exploring walking paths with his wife Susan, and visiting their six grandchildren. A little-known fact: In May 1994, Howard was featured—along with five others—on the cover of Kiplinger’s Personal Finance for an article titled “Secrets of My Investment Success.” Check out his previous articles. [xyz-ihs snippet="Donate"]

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. The ER prioritizes based on the severity of the health issue, not on who arrives first. You’d want the same if you were there for a heart attack. 2. Tell the truth. No matter how embarrassing your condition or the circumstances surrounding your accident, the ER staff has heard it all. By knowing the background, the doctors and nurses will be better able to help. 3. Any medical history you can bring will be useful. Arriving with a list of medications, current medical problems, past surgeries and the names of your physicians will speed things along. The longer the list, the more important the information is. If you have advance directives, bring those as well. If all your health care is provided within the same health care system, the ER might have access to your electronic medical records, but don’t count on it. 4. Visit the ER that’s in-network for your health insurance unless it’s a life-or-death situation. Showing up at an out-of-network ER has “major hassle” and “hefty bill” written all over it, though it may be necessary if you’re traveling. When picking health insurance, think about the emergency room you’re most likely to use. 5. The ER physician and staff don’t know how your insurance works and they don’t care. There are innumerable health plans out there, and each has its own network and limitations. By going to an ER, you’re conveying that you have an acute medical condition. They’re there to solve that problem, regardless of cost. 6. Surprise medical bills are real, but they can sometimes be avoided. The ER physician may refer a given condition to X hospital because it’s 15 minutes closer than Y hospital, which is equally capable. If X hospital isn’t in your network, speak up if you’re able. The same goes for surgeons or other specialists who drop by to consult. To find in-network providers, you might call the number on the back of your insurance card or use your phone to go to your insurance company’s website. [xyz-ihs snippet="Mobile-Subscribe"] 7. Helicopters are wildly expensive and a huge source of billing surprises. When necessary, they save lives, but understand that they may come with a significant out-of-pocket cost. If a helicopter is proposed, it’s reasonable to ask whether using slower ground transport is too medically risky. 8. The ER staff isn’t necessarily there to provide a definitive diagnosis. Their job is to determine whether your condition will kill you, and then prevent that from happening. If you arrive with chest pains, that might suggest five or so fatal conditions. Once those are ruled out, you’re safe to go home or to an inpatient floor for a follow-up to determine if you have, say, chronic indigestion. Medical problems on TV may be resolved in an hour, commercials included, but the real world often doesn’t work that way. 9. Despite the convenience of 24/7 availability, an emergency room should not be a substitute for your primary care physician. There’s value to your ongoing relationship with your primary care doctor that’s lost in the ER. An ER doctor may head down a diagnostic path that makes sense based on what she sees, but wouldn’t make sense if she had the background your doctor has. 10. We live in a world where we can review ratings for many products and services, and this is starting to be the case for physicians. You don’t have a choice of which doctor you’ll see in the ER. Still, evaluating them by previous patients’ reviews may be shortsighted. In the 1980s, hospitals started doing patient satisfaction surveys. I decided to share the physician-specific comments we received on our ER survey with each of our ER doctors. One consistently had the lowest satisfaction ratings. As I explored the reasons, I came to understand that he was very introverted and wasn’t one for small talk. No one ever said he was mean or inappropriate. Meanwhile, the ER nursing director rated him the highest for his medical skills. The other members of the medical staff all said they hoped he would be the one on duty if they arrived with a heart attack. Hospital administrators would love to only have doctors who are highly skilled and highly personable. Just remember, if your ER physician doesn’t bubble the way you think he should, his previous case may have necessitated telling a family that a child just died. Cut him some slack. Howard Rohleder, a former chief executive of a community hospital, retired early after more than 30 years in hospital administration. In retirement, he enjoys serving on several nonprofit boards, exploring walking paths with his wife Susan, and visiting their six grandchildren. A little-known fact: In May 1994, Howard was featured—along with five others—on the cover of Kiplinger’s Personal Finance for an article titled “Secrets of My Investment Success.” Check out his previous articles. [xyz-ihs snippet="Donate"]

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. Using an online calculator, I estimated my required withdrawals and dropped those amounts in. Currently, the six grandkids range in age from two-year-old twins to 11. My thought is to pay substantially all the cost of their junior and senior years. The kids are evenly spaced. Other than the twins, no two will have upper-class standing in the same year. I have 529 college-savings accounts for each child. Based on my current contribution levels, those accounts could be exhausted in their freshman years. Fidelity Investments’ college planning tool suggests that the average public university might cost $28,000 a year by 2031, which is when our oldest grandchild would be a freshman. The average private school might cost $64,000 by then. These costs inflate to $35,000 and $80,000, respectively, by 2038, when the twins are projected to begin college. Of course, these costs are only averages and could vary sharply depending on the specific school the grandchildren attend. On top of that, Fidelity is inflating current college costs by just 2.5% a year, which may be too conservative. For comparison, I’ve looked at the current cost of attending the private colleges my two children attended, as well as public universities in the states where the grandchildren live. After inflating these costs and comparing them to Fidelity’s results, I decided to increase my 2031 college cost estimates to $42,000 a year for a public school and $81,000 for a private school. I plan to use my 2030 required minimum distributions to open an investment account to pay future college costs. By investing in money market funds, certificates of deposit or Treasury bills, I could earn some interest before making college payments. Based on my projections, I estimate that I could provide up to $80,000 toward college in 2031. This will fund roughly a year of private college tuition, room and board. I inflated this amount by 2.5% a year to estimate the future college costs for the younger grandchildren. Eleven years of after-tax required minimum withdrawals will generate enough to cover two years of college for each grandchild. After that, my withdrawals can be used to support my needs in late retirement. [xyz-ihs snippet="Mobile-Subscribe"] If the grandchildren attend public schools, any extra money in their last two years of college could be used to repay student loans generated in their first two years. Some of the grandchildren might also earn scholarships that reduce their need for my money. If so, I have no problem giving them the planned money to jumpstart graduate school or their post-graduate life. There’s always a chance that some of the grandchildren won’t attend college or won’t make it to their junior year. My wife and I are flexible. Funding trade school, an apprenticeship or starting a business are all acceptable uses. Our goal is to help launch each grandchild into the adult world with minimal student loans or other debt. We’ll also have to consider disqualifying circumstances. We don’t like thinking about it, but our grandchildren might make choices that would make it unwise to turn over the money as planned. I could see holding it for them to see if they turn things around. We’ve not shared these thoughts with our children. I’m honestly not sure providing $160,000 per grandchild is a good idea. I would welcome thoughts from HumbleDollar readers. But it is a comfort to know the money is available to help them. No plan is perfect, of course. Here are three uncertainties that might affect my strategy: My projections are based on earning 5% a year on my rollover IRAs. Actual returns could affect the amounts available. Changes in the tax law could change my required withdrawal amounts. Our living expenses could increase to the point that implementing this plan would compromise our standard of living. These risks don’t mean we must abandon the plan entirely, but they could change the amount we can pay toward college. Once we commit to the first grandchild, we’ll have to be prepared to fund the other five. With the spreadsheet built, I can monitor growth in my IRA balances, changes in college costs and changes in the tax law. All this will allow us to zero in on a specific plan when the oldest hits high school. Then we can share it with the whole family. Watch this space for an update around 2027. Howard Rohleder, a former chief executive of a community hospital, retired early after more than 30 years in hospital administration. In retirement, he enjoys serving on several nonprofit boards, exploring walking paths with his wife Susan, and visiting their six grandchildren. A little-known fact: In May 1994, Howard was featured—along with five others—on the cover of Kiplinger’s Personal Finance for an article titled “Secrets of My Investment Success.” Check out his previous articles. [xyz-ihs snippet="Donate"]