The Cummings & Cummings Law Journal


Wednesday, September 10th, 2025


Calculator, magnifying glass, permanent marker, and federal income tax return

With tax season around the bend, I have compiled a few pointers on the mortgage interest tax deduction for U.S. taxpayers. What is a Form 1098? The 1098 is an IRS form that reports the amount of mortgage interest paid by a homeowner during the tax year. Lenders (banks and mortgage companies) provide this form

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Contemporary high-rise apartment building

Recently, someone shared this Reddit post with me and requested my take. The poster described how their “[l]andlord locked the thermostat in the middle of winter to ‘prevent’ the boiler losing pressure . . . It still drops pressure leaving us without heating or hot water every few days” and posted a photo of a

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Coins being deposited into blue piggy bank

Maximizing your Social Security benefits is not just about when you claim them—it also involves smart tax strategies to ensure you keep more of your hard-earned money. Many retirees unknowingly pay unnecessary taxes on their benefits, reducing their monthly income. In this article, we explore three proven tax strategies to help you optimize your Social

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Single-family home on a corner lot with a manicured lawn and small tree

House hacking has become a popular real estate strategy, particularly as home prices and interest rates have risen. By renting out part of a primary residence—whether a spare bedroom, a basement unit, or a duplex—homeowners can offset their mortgage costs and build equity at the same time. However, this hybrid approach to homeownership brings unique

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Picture of a mid-rise office building surrounded by palm trees

The pandemic fundamentally reshaped how organizations approach risk management, internal audit, and business resiliency. As businesses adapted to sudden disruptions, assurance functions evolved to meet new challenges, embracing real-time risk monitoring, enhanced data analytics, and more integrated compliance strategies. Now, with a new administration poised to implement regulatory changes—particularly around ESG disclosures, cybersecurity oversight, and

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Picture of a mid-rise office building surrounded by palm trees

Yesterday, I covered several residential real estate-specific federal income tax deductions available to current and prospective homeowners; in this post, I am broadening my focus to cover deductions from a general perspective. Navigating federal income taxes can feel overwhelming, especially when deciding whether to itemize deductions or take the standard deduction. For the 2024 tax

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Picture of a mid-rise office building surrounded by palm trees

As a tax attorney and CPA, I often work with homeowners who are navigating the complex world of federal income taxes. For homeowners, there are unique tax deductions available that can reduce taxable income and increase potential refunds. However, most of these deductions are only available if you itemize your deductions instead of taking the

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Road sign displaying the verbiage “Welcome to Florida” and “The Sunshine State”

I am receiving calls from current and prospective clients alike seeking to mitigate their payment of property taxes, particularly in light of the recent hurricane season. In fact, I was recently featured on WINK-TV news on this topic. I am summarizing, in an outline format, some of the considerations of current and would be homeowners

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Picture of a mid-rise office building surrounded by palm trees

Several of my clients are tax and audit practitioners operating small- and medium-sized compliance and advisory firms. In view of the forthcoming policy changes signaled by the incoming administration, here is a synopsis of some of the inquiries I have received from this audience in recent weeks: Following the inauguration of President Trump on Monday,

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Lately, I have been fielding questions from clients regarding the purportedly forthcoming ban on TikTok, particularly from a federal income tax perspective. Whilst the legal nuances underpinning the proposed ban and the Constitutional implications are complex, I am providing a brief synopsis below which addresses some of the key considerations from a U.S. income tax

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One of the most important decisions when starting a new business is choosing the legal entity type. The legal entity type you choose will affect many aspects of your business, including taxes. In Florida, the most common legal entity types for small businesses are limited liability companies (LLCs), partnerships, and corporations. In this blog post,

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Notepad with calculator and ink pen

When starting a new business, choosing the right legal entity type is important for many reasons, including tax considerations, liability protection, and flexibility. One option for small businesses is the S corporation, which is a special type of corporation that is taxed like a partnership or sole proprietorship. In this blog post, we will discuss

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What are the most common mistakes founders make?

Published on February 22, 2025

Starting a new business is exciting and challenging, and it can be easy for start-up founders to get caught up in the excitement and overlook potential pitfalls. However, failure to address these issues can lead to serious problems down the line. In this blog post, we will discuss common pitfalls that start-up founders make when

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Starting a new business can be a challenging and exciting venture, but it can also be fraught with legal pitfalls. Even the most well-intentioned start-up founders can make mistakes that can have serious legal and financial consequences. In this blog post, we will discuss the ten most common legal mistakes start-up founders make and ways

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Starting a business is challenging, but when foreign investors are involved, it can become even more complex. Foreign investors bring unique challenges and considerations that must be taken into account during the start-up process. In this blog post, we will discuss special considerations when a start-up has foreign (i.e., non-U.S.) investors. Understanding Foreign Investment Laws

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As start-ups grow and expand, they may need to hire additional personnel to help achieve their goals. However, there are important employment law considerations that start-up founders must take into account when making hiring decisions, including the choice of whether to classify contributors as employees or independent contractors. In this blog post, we will discuss

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Fundraising is an essential part of starting and growing a business, but it can also be one of the most challenging. Start-up founders must navigate a complex landscape of funding sources, investors, and regulations to secure the funding they need to bring their vision to life. In this blog post, we will discuss common problems

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As start-ups begin to grow and expand, they will inevitably be faced with the need to negotiate and enter into contracts with a variety of parties. These may include suppliers, vendors, employees, investors, and customers. It is important for start-up founders to understand the key contractual provisions that should be considered when negotiating these agreements

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Starting a new business is an exciting and challenging endeavor. One of the most important steps in starting a new business is filing the necessary documents with the Florida Secretary of State. In Florida, the process of forming a new business involves several steps and requires filing certain documents with the Secretary of State. In

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Starting and growing a business requires a diverse set of skills and expertise. While some start-up founders may have experience in certain areas, it is often necessary to hire professionals to help navigate complex legal, financial, and operational issues. In this blog post, we will discuss the number and types of professionals that a start-up

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