Healthcare costs aren’t a factor once you reach Medicare age. Many employers will gladly throw you a check for $134 a month to cover your Medicare premium. Much cheaper than insurance for even their youngest employees.

No, it really comes down to ageism. It’s rampant out there.

If you'd worked in some sort of highly skilled, narrowly focused career and lost that job for any reason whatsoever, it seems to be very difficult to get another job. Other areas, especially if you have basic computer skills and you're not looking for a high salary, are much better.

Ten years ago I found myself at age 60 needing to get back into the workforce that I'd been out of for a long time while raising children. Actually, I should go back about four years prior and mention I got a paralegal certificate from my local junior college, then had two part time paralegal jobs. It was after that my marriage came to an end.

I moved to another part of the country, got fired from the first two jobs I got, which was pretty devastating as I'd never before been fired. By then it was Christmas 2008 and between the time of year and that recession, getting work was almost impossible. I was working with three different placement agencies, calling them every week, and at one point was told that if I didn't have bookkeeping or accounting skills (I didn't) there was simply nothing out there.

Finally I was able to get hired at the local hospital doing outpatient registration. I did that, and then worked the information desk until I quit work altogether at age 65.

Well not quite altogether. A year or so later I saw an ad for a partime job, a clerical/administrative thing, at a local company. So I updated my resume and went in. They wanted to hire me on the spot. Unfortunately, their idea of part time was 30 hours a week, my idea was 20. So they asked if I'd consider doing some temp work for them in the future, and I said yes. Two different times they had me in, and it was a good experience. Other than having to be at work at 8am, since I'm not a morning person.

I do want to stress that I never had a real career, don't have a bachelor's degree which has certainly limited my employment possibilities. But contrary to the popular perception that no one every hires anyone over some arbitrary age, that's simply not true. Although I recognize that if you can't get the job you want and are trained for, it's certainly seems that way.

I think that not having a bachelor degree, nor a "real career" made you more attractive is not being too "overqualified." And, I think that the emphasis was on losing on the way to retirement.

From above:
Even just a few months out of work or living on a depressed salary without benefits can strain a senior’s finances as he struggles to cover mortgage payments, health care and other routine expenses. When a job is lost late in life and it takes a long time to find a new one, it can push back retirement by years or even erase the prospect of retirement completely.

Here are some examples from above

Greg Miller, 65 years old, a former environmental engineer and contract administrator, was laid off in 2017. He recently gave up looking for full-time work after sending out more than 400 résumés. “The heartbreak and the discouragement were just unbearable,” said Mr. Miller, who lives on Social Security and a part-time job. He shares a ranch house in Lansing, Mich., with three other men. “I am kind of working without a net here,” he said.

and..

Jill Short, 59, of Columbus, has an M.B.A. and previously worked for the federal government, a local utility and a technology subcontractor. The financial crisis made it tough to re-enter the job market after she took time off for foot surgery in late 2007. She had a few seasonal positions, but didn’t find another full-time job until 2012 and was laid off in a restructuring 4 ½ years later.

and..

Lisa Borthwick, currently age 60, was working as a graphic designer for a group of real-estate magazines when the financial crisis hit. She lost her job, then her Hernando, Fla., home, then her savings. She has no pension. She took on student loans to pay for her degree. A decade later, she is still struggling to recover.

“When I was sitting for interviews, they offered me $10 an hour,” she recalled. “They said most people your age only need supplemental income.”

Now living in the Midwest, she recently landed two part-time jobs—as an operations manager for a nonprofit and an administrator for a real-estate company. She said both jobs are fabulous, but she can’t afford her own apartment in a neighborhood where she would feel safe and doesn’t receive health insurance or other benefits. For the past two years Ms. Borthwick has rented a bedroom from a couple she met when, on the verge of homelessness, she put her dog up for foster care.

and..

Michele Langdon, 55, had worked for several startups and was employed by Hewlett Packard for nearly 20 years. In 2016, she was let go after the company sold the unit she worked for. Divorced and with two children, Ms. Langdon ran up $50,000 in credit-card debt. She relied on unemployment insurance, food stamps and a state program that helps the unemployed pay their mortgages during her 18-month job search.

Ms. Langdon figures she applied for roughly 500 jobs and eventually had to settle for a short-term contract position. A few months later, she was offered a full-time job as a program manager for a new data-center business at a different company. But the lengthy time out of work means she now expects to work until at least age 70.