The waiting area of the Pilsen Community Tax Clinic smelled like burnt coffee and damp winter coats. It was the third Tuesday in February 2026, and every folding chair was taken. I was there reporting on Chicago’s network of free Volunteer Income Tax Assistance sites when a man in his early sixties caught my attention — he was holding a manila folder thick enough to be a legal brief, running a thumb across the labeled tabs like he was checking inventory before a job.
That was Keith Fulton. He runs Fulton Green Works, a landscaping company on Chicago’s Southwest Side that he has built over eighteen years from a one-truck operation into a twelve-employee business. When I introduced myself, he shook my hand firmly and told me he’d been filing his own taxes since 1998. “I figured I was here just to get a second opinion,” he said. “I didn’t think there was much left to find.”
There was quite a bit left to find.
A Business Owner Who Thought He Had It Figured Out
By most external measures, Keith Fulton, 61, had done things right. Fulton Green Works generated roughly $340,000 in annual revenue. He and his wife Sandra owned a home in Bridgeport, carried minimal consumer debt, and had been contributing to retirement accounts for two decades. Keith described himself to me as someone who reads the fine print and checks the numbers twice.
But when I sat down with Keith in one of the clinic’s back rooms — a converted storage space with a folding table and two plastic chairs — the picture he described was considerably more strained than the surface suggested. His daughter Maya, now 19, was born with cerebral palsy and requires full-time in-home care. That care costs the family approximately $6,800 a month, or $81,600 a year, paid largely out of pocket after Medicaid coverage limits are reached each year.
Then, in August 2024, a severe storm caused significant roof and water damage to the Fulton family home. Keith filed a $47,000 claim — the first claim he’d made in sixteen years with the same carrier. Two months later, in October 2024, he received a non-renewal notice. His insurer was dropping him.
“I stared at that letter for probably twenty minutes,” Keith told me. “Sixteen years, never a claim, and the one time I needed them, they decided I was too much of a risk. I could not believe it.”
He eventually secured a new homeowner’s policy, but the premium jumped from $2,200 a year to $8,600 — an increase of $6,400 annually, seemingly overnight. Combined with a 2021 refinance that left him carrying a $589,000 mortgage balance on a home now worth approximately $710,000, the financial pressure had become a constant background noise in his life.
The Mortgage Overhang Nobody Mentions Aloud
Keith refinanced in late 2021 to pull equity for home modifications that would better accommodate Maya’s care — a wheelchair ramp, widened doorways, a modified bathroom. At the time, with rates still low and the equity available, it was a logical decision. By early 2026, with rates having climbed and his cash flow tighter than expected, the math felt different.
“I’m 61,” he said, setting the manila folder on the table between us. “I refinanced into a 30-year loan. That mortgage runs until I’m 91. That’s the thing that keeps me up at night — not the business, not even the insurance. Just that number.”
What Keith hadn’t fully accounted for was how much of that financial pressure might be partially offset through the tax code. His software had been steering him toward the standard deduction every year — not because the software was broken, but because he hadn’t been entering all of his eligible expenses. He was omitting a significant portion of Maya’s medical and care costs, assuming they either didn’t qualify or that the threshold was too high to clear.
According to IRS Topic 502 on medical expenses, taxpayers can deduct qualified medical expenses exceeding 7.5% of their adjusted gross income. For Keith, with an AGI of approximately $290,000, that threshold was $21,750. His actual qualifying expenses for Maya — specialized therapies, medical equipment, home care costs above the Medicaid cap, and adaptive devices — came to roughly $63,000 for tax year 2024 alone.
What the Volunteer Found in That Manila Folder
The VITA volunteer assigned to Keith’s case was a retired CPA named Gloria. She spent nearly ninety minutes with him going through every receipt, every statement, every document in that folder. I waited in the hallway and spoke with Keith immediately after. He walked out looking faintly stunned.
What Gloria found was a substantial pile of unclaimed itemized deductions. Keith had been entering only Maya’s direct medical bills — doctor visits and prescriptions — into his tax software each year. He had not included the portion of her in-home care costs that qualified as medical expenses, the adaptive wheelchair purchased in 2023, communication devices, or the costs associated with the medically necessary home modifications he’d made during the refinance.
There was also a significant issue with how Keith had been handling the Dependent Care Credit. Under IRS rules, the standard age cutoff of 13 does not apply to dependents who are physically or mentally incapable of self-care. According to IRS guidance on the Child and Dependent Care Credit, qualifying expenses for such dependents can reach up to $6,000, with the applicable credit percentage determined by income level. Keith had stopped claiming the credit entirely when Maya turned 14, not knowing the disability exception existed.
The Numbers That Changed His Spring
By the time Gloria finished her calculations, Keith’s tax picture had shifted in a way he hadn’t anticipated walking in. His itemized deductions — including mortgage interest, the dramatically higher insurance premium, Maya’s qualifying medical expenses, and other eligible costs — totaled approximately $74,500 for tax year 2024.
He had walked into that clinic expecting to write a check to the IRS for $3,400. He walked out with a return showing a refund of roughly $2,700 — a swing of approximately $6,100.
“I’ve been doing my own taxes for fifteen years,” Keith said, standing by the clinic door in his coat, still holding the folder. “I thought I knew what I was doing. And I did — I was just not asking the right questions.”
Relief That Does Not Erase the Underlying Pressure
A $2,700 refund is not a solution to a $589,000 mortgage. It does not bring Keith’s insurance premium back down to $2,200. It does not reduce the $6,800 a month his family spends ensuring Maya has the care she needs. I want to be precise about what it actually changed in his life.
What it did, Keith told me, was prevent one specific thing from getting worse at the worst possible time. “That refund meant I didn’t have to draw on the business line of credit this spring,” he said. “Every spring, I have cash flow issues because we’re ramping up for the season. Usually I tap the line. This year I didn’t have to. That’s not nothing.”
He was also, when we spoke, beginning to research Illinois property tax relief programs for homeowners who carry significant disability-related home modification costs — a separate process from his federal return. The Illinois Department of Revenue offers several exemptions for qualifying households, though applications are handled independently from federal filing.
Keith was candid about the guilt that shapes his financial decisions. He mentioned more than once that every spending choice related to Maya felt non-negotiable in a way that sometimes overrode his analytical instincts. The care costs, the home modifications, the adaptive equipment — none of it had ever been questioned. But somewhere in that same protective impulse, he had also stopped questioning whether he was claiming everything he was entitled to.
The VITA program, operated in partnership with the IRS, primarily serves households earning roughly $67,000 or below — but many individual sites, including the Pilsen clinic where I met Keith, extend free services to small business owners and higher-income filers navigating complex situations involving disability care, business deductions, or recent financial disruptions. According to the IRS VITA program page, certified volunteers are trained to identify credits and deductions that commercial software often misses without human review.
Keith told me he plans to return next February. He’s already started a new folder.
Related: Your IRS Refund Tracker Went Blank After Filing — Here’s What That Actually Means in 2026
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