Jeffrey T. Gross LTD, CPA

If you’d like to arrange for a transfer of wealth through multiple generations, consider a dynasty trust. Assets are taxed just once, when they’re initially transferred to the trust. There’s no estate or generation-skipping transfer tax due on any subsequent appreciation in value. A drawback is that the trust is irrevocable. This means it generally can never be revised. Call us at (773) 792-1575 for more details.

Will Social Security benefits be available when you retire? Good question. These benefits are unlikely to disappear entirely. But payments may be smaller, and the qualifying age for full benefits (currently 65 to 67, depending on your date of birth) may increase. So it’s critical to take advantage of tax-deferred retirement vehicles and to make age-appropriate investments that can help you accumulate adequate savings. Call us at (773) 792-1575 to discuss your retirement goals and ways to achieve them.

Does your business provide complimentary on-site food and beverages for employees? The rules for deducting certain business meals have changed. Beginning in 2026, employers generally can’t deduct 1) meals treated as de minimis fringe benefits, or 2) employer-provided meals that are excludable from an employee’s income and provided for the employer’s convenience on business premises. For the 2025 tax year, generally the former were 100% deductible and the latter were 50% deductible. Contact us at (773) 792-1575 to discuss whether this change will affect your company and how to plan accordingly.

If you’d like to help a charity for a period of time but ultimately benefit one or more heirs and potentially save gift and estate taxes, consider a charitable lead trust (CLT). You transfer assets to the irrevocable CLT and the charity receives payments from it for a term of years. When the term expires, the remaining assets are distributed to the CLT’s beneficiaries. The CLT assets can include publicly traded securities, real estate, business interests and even private company stock. Call us at (773) 792-1575 for more details.

Does your business use independent contractors? The reporting requirements for these workers differ from those for W-2 employees. For payments made in 2026, businesses generally must issue Form 1099-NEC, “Nonemployee Compensation,” to contractors paid $2,000 or more (up from $600 for 2025). The higher threshold may reduce your administrative burden because you could have fewer forms to file with the IRS. However, it doesn’t change your recordkeeping, worker classification or backup withholding responsibilities. Contact us at (773) 792-1575 to help ensure you’re prepared for the updated reporting requirements.

If you rent out your primary residence or vacation home for no more than 14 days, you don’t have to report the income. (But you can’t deduct related expenses, such as advertising and cleaning.) If you rent it out for more than 14 days, the income is taxable. And you may be able to deduct expenses such as utilities, repairs, insurance and depreciation. Exactly what you can deduct depends on personal vs. rental use. The rules are complex, but tax savings opportunities are available. Call us at (773) 792-1575 to learn more.

The IRS has issued final regulations on the tax deduction for qualified cash tips. The legislation commonly known as the “One Big Beautiful Bill Act” created the deduction of up to $25,000 per year for 2025 through 2028. Qualified tips generally refer to cash tips received by an individual in an occupation that “customarily and regularly” received tips on or before Dec. 31, 2024. The final regs list more than 70 eligible occupations. In addition to occupations previously listed in the proposed regs, the final regs add visual artists, floral designers and gas pump attendants. The final regs also provide clarifications to the definition of a qualified cash tip. For more details, call us at (773) 792-1575.

Business owners: If you’re only reaching out at tax time, you may be missing some valuable insights. Why stop at tax filings? Let us help you make smarter business decisions year-round — from improving cash flow to navigating economic uncertainty to planning for growth. Please call us at (773) 792-1575 to learn more about how we can support your strategic goals.

Starting in 2026, the tax rules for the personal casualty loss deduction are changing. While the deduction remains limited mainly to disaster-related losses, eligibility is expanding beyond federally declared disasters to include certain state-declared disasters. Because the rules are complicated and additional limits apply, review your situation with us. We can help determine whether you’re eligible for a casualty loss deduction. Contact us at (773) 792-1575.

Even when your finance and accounting (F&A) team seems to be firing on all cylinders, they may feel burdened with heavy workloads and tight deadlines. Bringing in an external accountant can ease the pressure on your internal team and keep your business running smoothly behind the scenes. If your accounting and bookkeeping workload is piling up, we’re here to help. Call us at (773) 792-1575 to learn how we can support your business.