The open enrollment window for ACA marketplace health plans closed on January 15, 2026 — a deadline that passed quietly for millions of self-employed Americans who either didn’t know it existed or, like Lorraine Lombardi, were still scrambling to figure out what they could actually afford. I met Lorraine on January 9th, six days before that window shut, inside a Navarro Pharmacy in Hialeah. She was standing at the consultation counter, asking a pharmacist whether her father’s blood pressure medication qualified for any manufacturer assistance programs. I was waiting behind her.
What started as an overheard conversation turned into a two-hour interview at a nearby coffee shop. By the time Lorraine ordered her second café con leche, I had filled most of a notepad. Her story is not a clean redemption arc. It is something messier and more honest — a portrait of a high-earning small business owner who, by the logic of most income charts, should have been fine, and wasn’t.
The Business Was Good. The Balance Sheet Was Not.
Lorraine Lombardi, 36, runs a residential landscaping company out of Miami that she founded in 2018. By 2024, the business was generating roughly $230,000 a year in gross revenue — strong numbers for a solo operator with a small crew. She owns her home in the Westchester neighborhood, which she bought in early 2021 for $574,000, putting down $60,000 and financing the rest at a 3.1% rate. Her monthly mortgage payment sits at approximately $2,760, not counting property taxes and insurance.
She is also the primary caregiver for her father, Eduardo, 71, who moved in with her in 2023 after a stroke left him partially dependent on daily medication and occasional home health visits. That context matters because it shaped every financial decision she made in the eighteen months before I met her.
In September 2024, Hurricane Helene’s outer bands brought sustained winds and flooding to parts of Miami-Dade. Lorraine’s backyard retaining wall collapsed, and water intrusion damaged the rear of her home, including her garage and a storage room. The total repair estimate came in at $51,400. She filed a claim with her homeowner’s insurer, received a payout of $38,700 after her deductible, and began repairs. Three months later, her insurer sent a non-renewal notice. They were leaving the Florida market.
She told me this with a flatness in her voice that made it clear she had already moved past anger into something like exhausted acceptance. “I knew it was coming,” she said. “Every neighbor on my street has had at least one insurer walk away in the last two years. I just thought I had more time.”
Florida’s Insurance Exodus and What It Cost Her
Florida’s property insurance crisis is well-documented. According to the Florida Office of Insurance Regulation, at least six insurers had halted new business or begun non-renewing policies in the state between 2022 and 2025, citing unsustainable claims exposure. The practical consequence for homeowners like Lorraine is a forced migration to Citizens Property Insurance — the state’s insurer of last resort — or to the small cluster of specialty carriers still writing policies in South Florida.
Lorraine got quotes from four providers in November 2024. The lowest was $9,200 annually. The highest was $14,800. She went with Citizens at approximately $10,100 per year — roughly $842 a month, more than triple what she had been paying before. That single cost increase added $6,700 to her annual expenses overnight.
The mortgage she took out in 2021 at a favorable rate had seemed manageable when Miami home values were climbing. By late 2024, however, comparable homes in Westchester were selling for roughly $540,000 — below what she paid. She was not underwater by a dramatic amount, but she had no equity cushion to draw on, and refinancing was not a realistic option at current rates. “I’m stuck in the house,” she told me, “which isn’t the worst thing except that it means the house has to keep performing, and right now the house is just taking money.”
Where the Health Coverage Cracked
As a self-employed business owner, Lorraine purchases her own health insurance through the ACA marketplace. In 2024, she was enrolled in a Blue Cross Blue Shield Silver plan through HealthCare.gov that covered both herself and her father as dependents. The premium was $1,140 per month — steep but manageable given her income. She received no premium tax credit because her estimated modified adjusted gross income for 2024 placed her above the threshold for meaningful subsidy.
When the property insurance costs spiked, she started reviewing every recurring expense. The health plan was, by dollar amount, the most obvious target. In December 2024, she downgraded to a Bronze plan for 2025, cutting her premium to $740 per month — saving $400 a month — but accepting a family deductible of $9,200 before the plan paid for most services.
Her father’s medications — a combination of an ACE inhibitor, a statin, and a low-dose anticoagulant — were running approximately $340 per month out of pocket on the new Bronze plan until the deductible reset in January. That figure is what brought her to the pharmacy counter where I found her. She was asking whether any of the three drugs had patient assistance programs or whether GoodRx pricing would get her below $200 combined.
The Prescription Assistance Search — and What She Found
The pharmacist that afternoon pointed Lorraine toward two options she hadn’t considered. The first was checking manufacturer patient assistance programs directly — some pharmaceutical companies offer income-based discounts that don’t require the applicant to be uninsured, only to demonstrate financial hardship. The second was the Medicare Part D Extra Help program, which Lorraine initially dismissed because she assumed Medicare was irrelevant to a 36-year-old. But her father, at 71, was potentially eligible.
Eduardo Lombardi had Medicare Part A from his prior work history, but had not enrolled in Part D when he turned 65 — a gap Lorraine said she simply hadn’t known to address at the time. “No one told us,” she said, with a tired edge that I recognized as the particular frustration of someone who feels they were failed by a system that expected them to already know the rules. Missing Part D’s initial enrollment period can trigger a late enrollment penalty, though Special Enrollment Periods may apply in certain circumstances, according to the Social Security Administration’s Medicare guidance.
When I followed up with Lorraine three weeks after our initial meeting, she had taken the pharmacist’s suggestion and called Medicare’s helpline. Her father was found eligible for a Special Enrollment Period due to a qualifying life event — his move into her home in 2023 may have triggered an earlier window she hadn’t used, but a SHIP counselor helped her identify a current pathway. He was enrolled in a Part D plan by early February 2026, with his monthly drug costs dropping to approximately $47 under the new plan’s formulary.
“That one phone call saved me almost three hundred dollars a month,” she told me. “Three hundred dollars that I was just hemorrhaging because I didn’t know what questions to ask.” There was something bitter in the way she said it — not gratitude, exactly, but relief filtered through the awareness of how long she had been losing that money unnecessarily.
The Outcome, Measured Honestly
Lorraine ultimately decided to stay on the Bronze ACA plan for herself — a choice she described as a calculated gamble. She is 36 and healthy, and the $400 monthly savings felt more urgent than the theoretical protection of a lower deductible. Whether that calculation holds through 2026 will depend on whether she stays well. She knows that.
The numbers look better on a spreadsheet than they feel in real life, Lorraine told me. The property insurance cost is still dramatically higher than it was two years ago, and the equity she expected to be building has stalled. She is paying down a mortgage on a house that has not appreciated, in a market where insurance is now a meaningful line item rather than an afterthought. “I built something real,” she said of her landscaping business. “But the ground it’s sitting on keeps shifting.”
What stays with me from those two hours in the coffee shop is not the dollar amounts — though the figures are specific enough to feel real — but the compounding nature of the pressure she described. Each individual problem had a partial solution. The property insurance had Citizens. The prescriptions had Part D. The health premium had a Bronze downgrade. But none of those solutions was free, and each one required Lorraine to know the right question before she could find the right door. She found most of them six months late.
Whether the decisions she made in January 2026 will look smart or regrettable by December is something neither she nor I can know yet. She is, as she told me on the way out, “trying to stay positive about it.” The trying was audible.
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