Richard Connor

THIS IS MY 150TH article for HumbleDollar. My first appeared on Aug. 12, 2019. I’m not sure when I became aware of the site, but it’s become an important part of my life. I’ve truly enjoyed the writing, along with reading the work of others and interacting with the editor, other contributors and readers.
For my 150th, I thought about looking back over the past five years and compiling a list of 150 observations.

HOW DO WE MEASURE societal wealth? And what triggered this thought?
I started pondering the issue early last year. I had a total left knee joint replacement in January 2023. Not long after, I was sitting in my living room with an ice pack on my knee, having just completed a strenuous set of stretches and exercises.
The room was being warmed by a modern gas fireplace, lit by a remote control. No wood to split,

JANE IS A SINGLE woman in her 80s, sharp and friendly. She’s a former state employee with a solid retirement income. Unfortunately, she’s suffered some health issues in the past few years that have forced her to make serious changes.
I became aware of her issues when she came into the local AARP TaxAide site where I volunteer. She was the last client of the day, and the other scheduled client had rescheduled, so she got our full attention.

WHAT WILL BE YOUR legacy? This is something I’ve given a lot of thought to—right down to the funeral instructions.
Something I’ve learned through hard experience: One of the greatest gifts we can give to our families is a well-organized and well-communicated estate plan. They’ll appreciate it when the time comes.
Too many of us wait until an emergency to try to get our affairs in order. A severe illness or death is stressful enough.

THE LONGER I SPEND in retirement, the more convinced I am of the benefit of reliable income. One of retirement’s most pronounced psychological shocks is the loss of a regular paycheck. After four decades of working, you get used to one coming in every two weeks. The occasional consulting paycheck, even a small one, makes me inordinately happy.
I’m fortunate to have a traditional defined-benefit pension. It built up over 31 years of working with a large aerospace engineering firm.

I KEEP SEEING THEM—overly complicated, overly expensive investment portfolios. The most recent belonged to a widow in her 70s, with modest earned income, Social Security benefits and about $5,000 in taxable fund distributions for 2023. She was someone I helped during the recent tax-filing season, when I was volunteering at an AARP TaxAide site in Monmouth County, New Jersey.
Her portfolio held about a dozen mutual funds, most of which I’d never heard of.

OUR INCOME TAX SYSTEM is based on voluntary compliance. Taxpayers are responsible for reporting all their income and paying the required taxes.
In assessing tax returns, the IRS differentiates between tax avoidance and tax evasion. Tax avoidance is “an action taken to lessen tax liability and maximize after-tax income,” while tax evasion is “the failure to pay or a deliberate underpayment of taxes.”
What are the major sources of tax evasion? Under-reporting income seems to be No.

I RECENTLY WROTE an article about our purchase of a new primary residence, and our plans for our existing beach house. On the same day, HumbleDollar published a companion article that I also wrote. That second piece discussed the tax implications—and complications—of converting a former primary home to a rental property.
We had purchased the new home using a mortgage, and our plan was to refinance the beach house and use those funds to pay off the mortgage on our new primary residence.

SOCIAL SECURITY retirement benefits are a critical source of income for many seniors. But as I’ve discovered from preparing tax returns, there’s a lot of confusion surrounding two key issues.
The first issue: the reduction in benefits that occurs when folks claim benefits before their full retirement age (FRA) of 66 or 67, but continue to work. This is the so-called earnings test. If folks are under their FRA for the full year, the Social Security Administration will reduce their benefits by $1 for every $2 earned above $22,320,

SAVINGS YIELDS SOARED in 2023—and all that interest income is now showing up on people’s tax returns.
Forbes published historical average money-market rates based on FDIC data. The average rate in 2020 and 2021 was 0.1%. That jumped to 0.15% in 2022 and 0.59% in 2023. But remember, those are averages, and it isn’t difficult to find higher yields. For instance, interest rates on high-yield savings accounts are up sharply since spring 2022.

ON OUR RECENT TRIP to Alaska, I was surprised by the number of solo women passengers. It turns out I shouldn’t have been.
According to a recent report from Road Scholar, a not-for-profit travel company geared toward those age 50 and older, a quarter of its travelers were single, with 85% of them women. That group included married folks traveling solo. It’s a growing trend. The Road Scholar study reported that 60% of the company’s solo travelers in 2022 were married.

VICKY AND I ALWAYS knew our retirement home would need to be near our two sons and their families, so we could be part of our grandchildren’s lives. It’s taken a few years and a pandemic, but we finally made that happen.
We purchased a new home in Monmouth County, New Jersey, in September 2023. We’ve now moved in, and we’re already enjoying more time with our grandsons. We’ve also met some very welcoming neighbors.

WE SOLD OUR PRIMARY residence in the Philadelphia suburbs and moved to our New Jersey beach home in March 2021. The sale allowed Vicky and me to take advantage of what’s arguably the most valuable tax break available to everyday Americans: the capital-gains tax exclusion on the sale of a primary residence.
But while the tax break is valuable, it comes with strict and often-confusing rules—and those rules may work against us now that we’ve moved home yet again.

WHEN I LAST REPORTED on our retirement journey, we’d decided to put our search for a second home on hold. Well, in the immortal words of Saturday Night Live’s Emily Litella, “Never mind.”
We looked at many properties in several communities earlier this year, but we didn’t find anything we wanted to purchase. We decided on a cooling-off period, while we pondered what our next step should be. We kept a casual eye on properties coming up for sale,

ALASKA FINALLY HIT the top of our bucket list. A number of friends had made the trip and returned with glowing reports of the scenery, wildlife and fresh seafood. Vicky and I each had our own No. 1 reason for the trip: She wanted to see whales, and I wanted to see the Northern Lights.
Alaska’s Inside Passage is often the destination for travelers headed to the 49th state. There’s a wide variety of ships that ply those waters,