David Cooper Archives - Walter Shuffain

Planning Ahead with Qualified Small Business Stock

Written by: David Cooper Why this matters: Qualified Small Business Stock (QSBS) offers one of the most powerful tax benefits available to business owners and investors: the potential to exclude millions of dollars in capital gains from tax. But taking advantage…

How the One Big Beautiful Bill Impacts Business Owners: A Strategic Overview

The One Big Beautiful Bill Act (OBBB), signed July 4, 2025, brings sweeping federal tax updates that will reshape your year-end planning. We’ve identified the provisions: bonus depreciation, Sec. 179 expensing, QBI deductions, new above-the-line breaks, and international rules that…

The One Big Beautiful Bill Becomes Law: A Detailed Tax Breakdown for 2025 and Beyond

On July 4, 2025, President Trump signed the One Big Beautiful Bill Act (OBBB) into law, enacting one of the most comprehensive tax packages since the Tax Cuts and Jobs Act of 2017. The legislation introduces permanent structural reforms to…

Distressed Real Estate Debt Restructuring: What Investors Need to Know

Written by: David J. Cooper, CPA and Mark Ravera, CPA Property owners and developers are facing growing financial pressure. Interest rates have more than doubled in recent years, operating costs continue to climb, and tenant demand remains inconsistent, especially for…

Proactive Tax Planning for Expanding Businesses

Growth is exciting as a business owner, but it also brings added complexity to your tax situation. Expansion may mean hiring new staff, entering new markets, or investing in new assets. Without proper planning, these changes can increase your tax…

Navigating Tomorrow: Year-End Tax Strategies for Business Owners

As we near year-end, proactive tax planning becomes more crucial than ever for businesses and family offices with complex tax portfolios. While 2024 hasn’t brought significant legislative tax changes, foundational tax strategies remain invaluable. With potential transactions and evolving state…

The Joys of Home Ownership: Balancing Financial Support and Tax Consequences with Real Estate Wealth Transfer Strategies

For high-net-worth individuals, the art of wealth transfer extends beyond merely providing financial assistance to future generations; it is about strategically positioning the next generation for personal success. Unfortunately, it also requires navigating a complex landscape of income, gift, and…

The Role of Tax Planning in Sustainable Business Growth

Written by: William Cooper, CPA For many business owners, taxes often represent a hurdle to clear rather than a strategic asset to leverage. However, those who look beyond mere compliance can unlock the transformative power of tax planning as a…

Begin Your Tax Planning Journey Here

Effective tax planning is essential in today’s business and personal financial landscape. As we quickly approach year-end, there is no time to waste. Businesses, individuals, and family offices should assess their 2023 and 2024 tax situations to uncover opportunities for…

Massachusetts Corporate and Individual Tax

Massachusetts Enacts Corporate and Individual Tax Changes

On October 4, 2023, Massachusetts Gov. Maura Healy signed H. 4104 to enact numerous business and individual tax changes. The more significant changes include adopting single-sales-factor apportionment for all corporate taxpayers, changing the sourcing of financial institution receipts from investment and trading,…

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