A certified letter from the City of Honolulu was waiting for Sandra May at the post office. Life had been chaotic since her car accident. Between her hospital stays, doctor visits, and convalescing at home, she hadn’t been able to pick up the letter.
Instead, she opened a copy of the letter that arrived in her regular mailbox.
Sandra stared at the piece of paper in her hands, transfixed by the numbers glaring back at her. Six hundred thousand dollars. That’s nearly how much Honolulu was demanding she pay as punishment for breaking the law.
What could this eighty-three-year-old widow have possibly done to warrant a fine of over half a million dollars?
Home in Hawaii
Sandra May moved to Honolulu in 1968 when her first husband was stationed there with the Navy. They loved the area so much, they never left.
For over fifty years, Sandra has lived in the same home, although she wasn’t always the owner. Originally, Sandra was a tenant, renting the home from a man who was also one of her real estate clients. While Sandra helped him list some of his other properties on the market, she was also trying to convince him to sell her the house she was renting.
Like many older people, Sandra struggles with the computer and was overwhelmed while listing her property online. She had no intention of breaking the city ordinance with her advertisement.
After multiple attempts and written offers were turned down, the owner eventually had to declare bankruptcy and finally agreed to sell Sandra the home.
Underneath the home was a small one-bedroom apartment where a long-term tenant lived before Sandra took ownership. After that tenant left, she continued to rent out the unit continuously from 1970 through the late 2010s.
Sandra was fortunate: Some tenants stayed for a year, others for several years, and one tenant even stayed for twenty years. And she was always happy to have the supplementary income, especially while she was raising her son. In the early 2000s, she was even able to retire from her career in real estate, knowing she could rely on the rent from her tenants downstairs.
But her financial situation took a turn when her second husband’s health began deteriorating.
In 2019, after suffering from dementia and Parkinson’s disease, Sandra’s second husband passed away. Sandra had been his caretaker for the last two years of his life, tending to his every need. When he died, she suddenly found herself widowed, living alone, and relying solely on Social Security checks to get by.
At the time, the downstairs unit was empty, and Sandra was struggling to find renters, which she badly needed to help her make ends meet. To ease her search, she decided to list her property on online rental platforms.
Meanwhile, Honolulu was busy cracking down on short-term rentals.
The First Violation
By 2019, short-term rentals—stays fewer than 30 days—were illegal in Honolulu. But under a new ordinance, the fines for violating the law increased from $1,000 per day of noncompliance to a whopping $5,000 per day of noncompliance for initial violations. For recurring offenders, the fine could go as high as $10,000 per day.
It wasn’t just the severity of the fines that increased. For the first time, the ordinance also made it illegal to advertise a rental for stays of fewer than 30 days. If caught breaking the rule, violators received a notice from the City giving them seven days to remove the listing, along with fines ranging from $1,000 per day of noncompliance to $10,000 per day.
Shortly after the new ordinance went into effect, Sandra received a violation notice from the City in November 2019.
To say that Sandra is not tech savvy would be a vast understatement. Like many older people, she struggles with the computer and was overwhelmed while listing her property online. She had no intention of breaking the city ordinance with her advertisement.
She quickly worked with the online rental platform to change her listing’s settings so that it only showed availability for stays of 30 days or longer. Once the company assured her the problem had been resolved, she left the settings untouched for years. Truth be told, even if she had wanted to change them, she wouldn’t have been able to without assistance.
With the listing now in compliance, she had one less thing to worry about.
Then COVID hit.
The Second Violation
When the pandemic began, Sandra had tenants living downstairs. Shortly thereafter, the rental period came to an end, but the tenants refused to leave. For nearly two years, Sandra did not see a dime from her renters, even though they had received COVID rent assistance from the government. To make matters worse, a COVID-era eviction moratorium prevented Sandra from evicting the tenants from her own property.
Her hands were completely tied.
Sandra describes this period as a “disaster” financially, as she struggled to stay afloat without any income aside from collecting Social Security. When the eviction moratorium finally lifted in 2021, Sandra got a restraining order against the tenants and began the process of evicting them from her property.
With her unit now available to rent, she reactivated her online listing without making any changes to the 30-day minimum settings.
In June 2023, Sandra received a second violation notice from the City.
She was baffled. She hadn’t touched the settings on her listing in years. Sandra contacted the rental platform for help once again. The problem was fixed and Sandra alerted the City.
The City acknowledged that the listing was fixed, but because this was a repeat offense, she would have to pay a $10,000 fine.
However, a month after she learned of the fine, the City told Sandra that her previous violation from 2019 was actually an error. When the City issued Sandra the $10,000 fine, it was predicated on the 2021 violation being her second offense. Now that the first offense was nullified, Sandra believed the fine was also void.
From Bad to Worse
In March 2024, Sandra was badly injured in a car accident, landing her in the hospital for several days. After her release, she spent the next several weeks in and out of rehabilitation. Less than one month later, she underwent vascular surgery in the hospital, only to be hospitalized yet again just a few days later.
Over the following month, her life was filled with trips to the emergency room, urgent care, follow-up appointments, and more rehab for her injuries.
She stared down at the $590,000 fine printed in the copy of the certified letter.
What Sandra didn’t know was that the same day as her surgery, the City issued her a third violation notice and order for advertising for periods of less than 30 days. In their correspondence, the City warned Sandra that she needed to correct the online listing immediately, and until it was fixed, she would be fined $10,000 per day. Failing to fix the listing would result in the matter being referred to the prosecuting attorney’s office for criminal prosecution. She was also given a 30 day window to appeal to the City’s order.
Sandra was trying to recover while living alone without anyone to help her. Checking the mail regularly was not a priority. She was just trying to make it through each day.
Nearly two months went by before Sandra learned of the third violation notice and the order. By this time, the appeal window had closed.
She called the online rental platform. The customer service representative discovered an internal error in the system and promptly corrected the mistake. Sandra immediately called the City to let them know the listing had been fixed.
A Crushing Blow
“You’ve got to be kidding me” was the first thought that came to Sandra’s mind when she stared down at the $590,000 fine printed in the copy of the certified letter.
It had been over a year since the City contacted her about the third violation. She was under the impression the matter had been resolved. Yet, there she was, scrambling to figure out how to pay a fine she simply couldn’t afford. “I didn’t know what I was going to do,” Sandra later recalled.
After the initial shock from the fine subsided, Sandra took a closer look at the letter. The City confirmed that while the violation in question had been resolved, it took fifty-nine days to correct, leaving Sandra on the hook for $10,000 for each day of noncompliance.
If she did not pay the $590,000 fine immediately, the City could initiate legal proceedings to collect the fine, which included filing an administrative lien on the property.
But it didn’t stop there.
Sandra was also barred from accessing city services, like renewing her driver’s license and registering her vehicle. Unable to renew her license, Sandra was dependent on other people to help her get to her appointments and run errands.
The Lawsuit
One of the first things Sandra did after learning about the fine was to take down her rental listing. She couldn’t risk another internal error. But without the income from the rental unit, she was not sure how she can financially survive.
Faced with the prospect of losing her home and bankruptcy, she decided to talk to an attorney, who directed her to Pacific Legal Foundation.
In May 2026, Pacific Legal Foundation and Sandra May filed a lawsuit against Honolulu. The Constitution protects individuals from excessive fines by ensuring that punishments are proportional to the offense committed.
Sandra is no hardened criminal. She never intended to advertise her property for less than thirty days. And she did everything in her power to ensure that the listing error was fixed. But none of it mattered. The City still slapped her with fines that far exceed her ability to pay.
At eighty-three years old, it’s unlikely that Sandra ever would have recovered from the financial blow of a $590,000 fine.
But now she won’t have to. Shortly after Pacific Legal Foundation filed Sandra’s case, the City backed down. Honolulu offered Sandra a settlement that reduced her initial fine by 95 percent and resolved all other claims against her. Sandra accepted and happily dismissed her lawsuit.
“We are thrilled with this win for Sandra May,” said Pacific Legal Foundation attorney Loren Seehase. “This outcome reaffirms that fines must be proportionate to the alleged offense, not whatever the government thinks it can get away with demanding, and ensures Sandra can keep her home, which the City’s initial demands would have forced her to sell.”
As for Sandra, she is thrilled to be putting this entire chapter behind her.
“Winning this case is an enormous relief,” Sandra says. “But most of all, I’m grateful that at the lowest point in my life, God provided exactly what I needed by bringing Pacific Legal Foundation into my life.”
