When staff drive personal cars or the business rents a sedan for errands, personal auto and rental contracts often leave the company exposed. Hired and non-owned auto (HNOA) is the gap Chicago shops miss.

If you pay owner-operators, shops, or freelancers $600 or more, Form W-9 belongs in the file before year-end. Waiting until January is how Chicago-area fleets miss Form 1099-NEC and invite IRS notices.

A personal auto policy is built for personal trips. When the same car hauls cargo, carries paying passengers, or runs errands for the company, many claims get denied. Here is the coverage gap Chicago-area owners miss.

Calendar-year partnerships and S corporations on extension must file Form 1065 or Form 1120-S by Monday, September 15, 2026. Here is what Chicago-area fleet owners should lock down before the late-filing meter starts.

Your third 2026 federal estimated tax payment is due Tuesday, September 15. For Chicago-area trucking, logistics, and livery owners, 100% bonus depreciation under the OBBBA can change this year’s tax, but it does not rewrite last year’s safe harbor.

Trump Accounts (under new IRC Section 530A) are a specialized type of traditional individual retirement account (IRA) designed for minors. They allow contributions from parents, guardians, relatives, employers, and certain other sources, with investments focused on low-cost U.S. equity index funds (e.g., those tracking the S&P 500) to promote strong compound growth.

The OBBBA delivers permanent changes that can reduce your 2025 tax liability by 20-30% if implemented correctly.

Entrepreneurs in livery services, think taxis, limousines, and ride sharing fleets, and trucking/logistics companies, take note: The One Big Beautiful Bill, signed into law on July 4, 2025, has reinstated 100% bonus depreciation as a permanent fixture in the U.S. tax code.

The OBBBA revives a form of personal auto loan interest deductibility, not seen since the 1980s, to encourage new vehicle purchases while supporting U.S. manufacturing. This above-the-line deduction, reported on Schedule 1 (Form 1040), can be claimed whether clients itemize or take the standard deduction. It covers interest paid on loans for new, U.S. assembled passenger vehicles, capped at $10,000 per year, with excess interest carrying forward within the 2025–2028 period. The Joint Committee on Taxation estimates this provision will cost the Treasury $31 billion, underscoring its value for taxpayers.

Happy International Women’s Day! Today, we celebrate the social, economic, cultural, and political achievements of women around the world. At our CPA practice/Insurance agency, we recognize the important role that women play in shaping the future of our industry and the world.