The open enrollment window for 2026 ACA marketplace plans closed in mid-January, but the Special Enrollment Period — triggered by qualifying life events like income changes or loss of coverage — remains available year-round. That timing matters more than most people realize, and no one illustrated it more clearly to me than Theresa Bianchi.
I first heard Theresa’s name in February, during a volunteer delivery shift I joined with a local Milwaukee Meals on Wheels chapter. A fellow volunteer, a retired accountant named Gerald, mentioned her almost offhandedly between stops. “You should talk to my neighbor Theresa,” he said. “She’s a real estate agent. Sharp as a tack. Had a hell of a year and figured something out that I wish I’d told her sooner.” He passed along her number. Two weeks later, I was sitting across from her at a corner table in a Bay View coffee shop, her property listings spread across half the table and a cup of black coffee going cold beside her.
The Year the Market Turned and the Rent Bill Arrived
Theresa Bianchi is 61 years old, has worked as an independent real estate agent in the Milwaukee metro area for nineteen years, and has never had an employer pay for her health insurance. That detail sounds mundane until you understand what it costs to be a self-employed individual buying coverage on the open market without any help.
Through most of her career, Theresa earned well. In 2022 and 2023, her gross commission income topped $115,000. She paid for a solid individual health plan — $698 a month in 2023 — and she didn’t think twice about it. She was doing fine. Then 2024 arrived.
The residential real estate market in Milwaukee, like most of the country, stalled under the weight of elevated mortgage rates that persisted through much of 2024. Transactions slowed. Deals that Theresa expected to close in spring and summer either fell through or pushed into the following year. Her gross commission income for 2024 came in at approximately $67,400 — a drop of nearly $50,000 from the prior year.
At the same time, her landlord sent a lease renewal notice. Her one-bedroom apartment in the Third Ward, which she had rented for $1,800 a month, was being re-listed at $2,340. A 30 percent increase. “I’d been there six years,” Theresa told me. “I thought that counted for something. Apparently it doesn’t.”
She also helps pay her younger brother’s tuition at UW-Milwaukee — roughly $6,800 a year — because their parents are no longer able to. “He’s twenty-three and he’s going to finish,” she said, with the quiet finality of someone who has already decided and doesn’t need to discuss it further.
The Assumption That Cost Her Thousands
For most of her career, Theresa had operated on a reasonable-seeming assumption: she made good money, so she wouldn’t qualify for subsidized health coverage. The ACA’s Premium Tax Credit, she figured, was for people who earned much less than she did. She never looked into it seriously.
That assumption was understandable — but it was also expensive. The Premium Tax Credit under the Affordable Care Act is available to individuals whose household income falls between 100 percent and 400 percent of the federal poverty level, with enhanced subsidies — extended through legislation in 2021 and maintained since — available even above that threshold on a sliding scale. For a single filer in 2024, the 400 percent FPL ceiling sat at approximately $58,320. Theresa’s net self-employment income, after business deductions, came in closer to $51,000 — well within the range.
“Nobody ever explained to me that it wasn’t about my gross income,” Theresa told me. “I was filing my own taxes for years. I knew I could deduct health insurance premiums. I just never connected it to whether I might also qualify for a credit.”
She found out the way a lot of people find out things too late: during a conversation with someone who happened to know. Her accountant — whom she finally hired after years of filing solo — flagged it when she brought in her 2024 documents in early February 2025.
What the Numbers Actually Looked Like
When Theresa’s accountant ran the numbers, the picture shifted considerably. Her gross commissions of $67,400 were reduced by legitimate business expenses — mileage, marketing, professional dues, office costs — and by the self-employed health insurance deduction of $8,376 (her total premiums paid in 2024). Her MAGI came in at approximately $51,200.
At that income level, according to Healthcare.gov’s eligibility guidelines, Theresa’s required contribution toward a benchmark silver plan premium is capped at a percentage of her income — meaning the federal government covers the gap between what she’s required to pay and what the plan actually costs. The result: a $4,200 Premium Tax Credit reconciled on her 2024 federal return.
She hadn’t enrolled through the marketplace during open enrollment, so she couldn’t receive the credit in advance as a monthly reduction to her premium. Instead, it came as a lump sum credit on her return. “I got a refund I wasn’t expecting,” she said. “And I also realized I’d been overpaying for years.”
The Harder Reckoning: What She Still Carries
The $4,200 credit helped. But Theresa was careful with me — she didn’t want to frame her story as a clean rescue. The rent increase stuck. She moved in September 2024 to a smaller apartment in Riverwest, at $1,950 a month, which solved the immediate problem but added the cost and disruption of moving. Her brother’s tuition bill didn’t go away.
And she is acutely aware of the year ahead. Real estate commissions in the Milwaukee market have remained soft into early 2026. She’s projected her 2025 income at roughly $74,000 gross — higher than last year, but not a return to her peak years. She enrolled through the Wisconsin ACA marketplace for 2026 coverage during open enrollment, this time with advance premium tax credit payments reducing her monthly premium from $812 to approximately $463.
“I think about what I paid over the years I didn’t look into this,” she said. She paused, turning her coffee cup in a slow circle. “That’s the part I keep coming back to. Not anger, exactly. More like — you just wish someone had sat you down earlier.”
There’s a particular frustration in her voice when she talks about the self-employed experience more broadly. She pays both the employee and employer share of FICA taxes — a 15.3 percent self-employment tax on net earnings. She manages her own retirement contributions. She tracks every deductible mile. And for years, she managed her own health insurance without knowing the full landscape of what was available to her, because no HR department had ever handed her a benefits packet.
What Theresa’s Story Reflects About a Much Larger Gap
Theresa’s situation isn’t unusual — it’s representative. According to KFF research on non-group insurance markets, self-employed individuals consistently underutilize marketplace enrollment and tax credits, often because of income volatility and lack of awareness. The IRS’s own data shows a significant portion of eligible filers fail to claim the Premium Tax Credit at all in years when their income qualifies.
The self-employed health insurance deduction, which allows qualifying individuals to deduct 100 percent of health, dental, and long-term care premiums from gross income before calculating MAGI, is a separate but interacting provision. Understanding how these two mechanisms work together — and in which order they must be calculated — requires navigating a circular computation that even tax professionals find cumbersome. The IRS Publication 974 dedicated to Premium Tax Credit and self-employed health insurance deduction interaction runs to dozens of pages.
Theresa isn’t a low-income worker who fell through a safety net crack. She is a high-earning, financially literate professional who missed a benefit because the system is genuinely hard to navigate without guidance. That distinction matters when thinking about who these programs serve — and who they fail to reach.
When I left Theresa that afternoon, she was heading back to a showing in Wauwatosa. She had a new listing, her first strong spring lead of the season. She seemed steadier than the woman Gerald had described to me six weeks earlier — not because the pressure had lifted, but because she had stopped operating on assumptions she’d never tested.
“I’m not waiting for things to sort themselves out anymore,” she told me as she gathered her folders. “I ask more questions now. About everything.”
That’s a harder lesson than any tax credit, and it doesn’t come with a refund check. But watching Theresa walk out into the gray Milwaukee afternoon, I thought it might be worth more.
Vivienne Marlowe Reyes is a Senior Tax & Stimulus Writer at American Relief. This article is for informational purposes only and does not constitute financial, tax, or legal advice. Consult a qualified professional for guidance specific to your situation.
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