The house, the baby, and the W-4 fix — everything in one place for filing season.
Verified Sept 29
Withholding: on track
Lev’s Sept 15 pay stub checks out — the W-4 is on single rates, the right setting for a two-earner household, on pace for ~$18,100 withheld in 2026. Blair’s was fixed at the same time. The October estimator run is now a 25-minute confirmation with both stubs, not a rescue mission — plus the $2,200 baby credit lands in your favor.
Free, no login, takes ~25 min. Have both of your most recent pay stubs handy.
What changed in 2026
🏠 The house — closed Oct 15
Partial-year mortgage interest is deductible (paid Oct–Dec)
Property tax: likely $0 deductible in 2026 — Illinois bills in arrears, so the 2026 bill is paid (and deducted) in 2027
The ~$15,149 seller tax proration at closing reduces your cost basis — it is not a deduction
Check the final Closing Disclosure for points — points on a purchase mortgage are generally deductible in the year paid
👶 The baby — due Dec 9
$2,200 Child Tax Credit for 2026 ($1,700 refundable), even for a December birth — a child born during the year counts for the whole year
Needs a Social Security number before you file — apply at the hospital
The hospital worksheet needs the legal name settled, including the surname decision
Night nurse? (3–4 nights/week, 6–10 weeks, at your house) — if hired directly she’s likely your household employee: EIN, Schedule H, and a W-2. Through an agency, she’s their employee and there’s nothing for you to file. Confirm with the CPA.
Key 2026 figures
Item
Amount
Mortgage interest, 2026 (est.)
~$4,350
Property tax paid in 2026 (est.)
$0
SALT deduction cap (MFJ)
$40,400
Standard deduction (MFJ)
$32,200
Child Tax Credit
$2,200
CTC phaseout starts (MFJ)
$400,000 MAGI
Lev’s 2026 withholding pace
~$18,100
Mortgage interest estimate: Oct 15–31 prepaid at closing (~$1,570) + November interest paid Dec 1 (~$2,780). December’s interest is paid Jan 1, so it counts for 2027. The 1098 arriving in January is the final word — update this line when it lands.
Itemize vs. standard, 2026
Your likely itemized total is ~$4,350 interest + a full year of Illinois income-tax withholding — almost certainly below the $32,200 standard deduction. Plan on the standard deduction for 2026, and run the real numbers at filing time.
2027 flips the other way
A full year of interest (~$33,400) + the 2026 property-tax bill paid in 2027 (~$18.6k) + state income tax will push you well past the standard deduction. Itemizing should win big in 2027.
Withholding checklist
Documents for filing season
Ticking a box saves on this device only — same as the other checklists.
CPA or self-file?
Decision for the Oct 17 money meeting — leaning toward Greg Ciokajlo (Ciokajlo, Hein & Associates), who handled Blair’s gift trust K-1s. The case for a CPA this year: first year as homeowners, a new dependent, a possible night nurse on Schedule H, Illinois quirks, and last year’s under-withholding. The case for self-file: otherwise straightforward W-2 income. Questions for Greg: night-nurse classification (agency vs direct hire), Yelena’s classification, and the house/baby items above. This page plus the document checklist is your meeting packet.
2027 preview
Yelena starts in April — at her house, not yours. That likely makes her self-employed, not your household employee: no Schedule H, no EIN, no employer payroll taxes — she handles her own self-employment tax. Confirm the classification with the CPA, and get her TIN so the payments can count toward the Child and Dependent Care Credit.
Full-year homeowner deductions — itemizing should beat the standard deduction by a wide margin.
Illinois Property Tax Credit: 5% of Illinois property tax paid on your principal residence (Schedule ICR, nonrefundable) — kicks in on the 2027 Illinois return, when you actually pay property tax.