Chicago cost segregation, made simple.

No, and this is one of the most commonly misrepresented points about Illinois state tax treatment. While Illinois starts state taxable income from federal taxable income and applies the flat 4.95% rate, the Illinois Income Tax Act (35 ILCS 5/203) requires addition modifications for federal bonus depreciation with subsequent subtraction modifications. The practical effect: your federal §168(k) acceleration under OBBBA's 100% bonus captures cleanly in Year 1 on the federal return, but Illinois requires the state-side acceleration to be spread across multiple Illinois tax years rather than concentrated in Year 1. The total Illinois benefit over the property's holding period equals what full conformity would produce, but the timing differs. Verify current-year Illinois treatment with your CPA, IL bonus depreciation rules have been adjusted multiple times in recent years. This makes Illinois materially less attractive than fully-conforming states (Colorado 4.40%, Utah 4.65%) for Year-1 cash, though the total federal-plus-state benefit over the hold period is similar.

Generally not in Chicago city limits in any way that supports the typical absentee §469 STR-loophole strategy. Chicago's Shared Housing Ordinance requires STR registration, restricts non-primary-residence absentee whole-unit STR operation, and imposes density caps in many residential zones. Adjacent suburban Cook County jurisdictions (Oak Park, Evanston, Skokie) and DuPage County (Naperville, Wheaton, Downers Grove) operate distinct STR regimes, some more permissive. For Chicago-resident investors specifically wanting §469 STR-loophole treatment, the practical path is to acquire property in adjacent permissive jurisdictions or pivot strategy to LTR + real-estate-professional status.

Each unit has its own kitchen, bath and appliance set, and those finishes and appliances are 5-year property; fencing, paving and landscaping are 15-year. The masonry shell, roof, boiler and central electrical service stay in the 27.5-year building. Our published reclassification band for a two-flat (duplex) is 8–21% of depreciable basis, typically 15%; a three-flat (triplex) is 8–26%, typically 17%. Where a building lands depends mostly on its finishes (carpet and vinyl reclassify, hardwood does not) and on documented renovation cost.

Neither reliably wins on reclass-as-percent-of-purchase. Our published bands for pre-war Chicago two-flats and three-flats in Logan Square, Avondale, Pilsen, and Bridgeport are 8–21% (two-flat) and 8–26% (three-flat); the multi-unit FF&E + renovation pool dynamic described above is what moves a building toward the top of its band. Downtown South Loop and West Loop condos carry higher land allocation (32%) reflecting the downtown-adjacent premium. Absolute dollar deductions are larger on the small-multifamily because basis is larger per total transaction ($425K–$685K for two-flat/three-flat vs $485K–$685K for single condo). For BRRRR portfolio operators, small-multifamily is the typical optimal target.

Not directly, the ordinance applies to STR operations, not long-term rental. LTR investors in Chicago operate under standard §469 passive-loss rules. The §469 STR-loophole that converts passive losses to active deductions doesn't apply to LTR property anywhere, so Chicago's STR restriction doesn't change the LTR cost-seg math. What matters for LTR investors is whether they can use cost-seg passive losses against passive rental income from other holdings, or whether they qualify as real-estate professionals under §469(c)(7) to convert losses to active W-2 offset. For high-volume Chicago BRRRR operators with 5+ properties, real-estate-professional status is typically achievable.

Usually not. Most residential studies, including two-flats, three-flats and condos, are prepared remotely from your closing documents, property records and photos, so there is no walkthrough to schedule. If an in-person site visit makes sense for your property, it is priced as its own line and you see it before you order.

Land cannot be depreciated, so every study sets it aside first. For Cook County properties the Cook County Assessor's split between land value and building value is a common starting point, and your report states which source the land figure came from. The Assessor reassesses one-third of the county each year, so City of Chicago values are refreshed on a three-year cycle.

Usually the next business day after you order and upload your documents. The study is delivered online as a CPA-ready PDF with the component schedule, depreciation tables and methodology.