Caitlin See, MPA, Author at Think Outside the Tax Box

AUTHOR SPOTLIGHT

Caitlin See, MPA

Caitlin See is a personal finance writer with seven years of experience. She’s written hundreds of articles about student loans, budgeting, insurance, mortgages and retirement planning for financial brands, including Student Loan Planner and The Plutus Foundation. She has a Master of Public Administration (MPA) and spent many years working for local government and nonprofit organizations throughout Texas and California. When she’s not writing about money, she’s wrangling her two little ones and rescuing as many dogs as possible.

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What You Need to Know About the Proposed Trump Savings Accounts

Tucked inside the narrowly passed “One Big Beautiful Bill Act,” President Trump’s sweeping tax and spending package, is a provision that’s drawing media attention: the creation of a new tax-deferred investment account called a Trump Account. A proposed $1,000 “baby bonus” tied to the account only adds to the intrigue. While the reconciliation bill primarily focuses on extending the 2017 tax cuts and reshuffling federal spending priorities, this unexpected addition could offer new planning opportunities for taxpayers.

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Is Student Loan Forgiveness Taxable? It Depends…

Is student loan forgiveness taxable? Yes. No. Maybe. Sometimes. It primarily depends on the student loan forgiveness program. But like everything else with student loans, there are a number of other factors at play. Why make it easy when you can thoroughly confuse taxpayers, federal student loan servicers and financial planners for years to come? Keep reading to learn when student loan forgiveness might be tax-free and how to prepare your clients for taxable loan forgiveness.

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How to Help Your Clients Maximize College Financial Aid

College tuition continues to climb, and for many families, financial aid can make or break their ability to afford their child’s higher education dreams. What most don’t realize is that their tax return — filed long before students even begin applying for college — plays a major role in determining how much financial aid they’ll receive. This is where you come in. Tax professionals and financial planners are uniquely positioned to help clients qualify for more college financial aid. But only if you know what to look for.

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How to Help Your Clients Lower Their Student Loan Payments

There are roughly 42.7 million federal student loan borrowers as of Q4 2024, creating an opportunity to provide additional insight to your clients beyond tax preparation. By leveraging certain tax and repayment strategies, you can help your clients reduce their tax liability and lower their student loan payments in one strategic swoop. Here’s how.

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Breaking Down Tax Benefits for Higher Education

With the rising cost of higher education and greater reliance on student loans, taxpayers are looking for every opportunity to ease the financial burden of earning a degree. Fortunately, several higher education tax benefits are available to help offset the high cost of tuition, student loans and other education-related expenses. However, certain eligibility requirements — such as income limits and tax filing status — often trip up taxpayers along the way. Understanding the nuances of these tax benefits for higher education can ensure your clients take full advantage of available tax savings.

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CURRENT EDITION

OBBBA Rundown: Provisions Affecting Individuals for 2025

Enacted into law on July 4, 2025, the One Big Beautiful Bill Act is the biggest set of tax law changes since the 2017 Tax Cuts and Jobs Act (TCJA). The provisions discussed in this article impact individual taxpayers for tax year 2025 and must be considered immediately for proactive tax planning purposes, future tax withholding, and estimated tax payment calculations. Clients have questions, and we can generally give them the answers they seek; however, some will require future IRS guidance for complete clarity.

OBBBA Rundown: Provisions Affecting Businesses for 2025

Enacted into law on July 4, 2025, the One Big Beautiful Bill Act is the biggest set of tax law changes since the 2017 Tax Cuts and Jobs Act (TCJA). The provisions discussed in this article impact business taxpayers for tax year 2025 and must be considered immediately for proactive tax planning purposes, future tax withholding, and estimated tax payment calculations. Clients have questions, and we can generally give them the answers they seek; however, some will require future IRS guidance for complete clarity.

Big, Beautiful, and Oh So Salty: SALT and the OBBBA

The SALT cap has been one of the most argued pieces of the One Big Beautiful Bill Act as it has been making its way toward passage. Actually, tax professionals and politicians have been talking about the SALT cap (and looking for ways around it) since it was enacted as part of the Tax Cuts and Jobs Act. As most of you are aware, most TCJA provisions were set to expire at the end of 2025, including the SALT cap. We take a look at where they stand now.

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  • How to Pay Less Tax on S Corporation Distributions

    Most taxpayers understand that having an S corporation often eliminates the so-called “double tax” issue C corporations pose. However, the majority of S corporations begin as C corporations and the activity that occurred during the time it was a C corporation will determine how and when to tax distributions from the S corporation. C corporations cannot avoid double taxation on profits simply by electing to be treated as an S corporation (yet there are many other ways to save this double tax on C corporations, stay subscribed to learn about them). Withdrawing C corporation profits even when it later becomes an S corporation can create an extra tax. Here’s how to avoid that.

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    COVID Tax Relief Allows Companies to Make Tax-Free COVID-19 Payments to Employees

    For a business owner, almost nothing in life is more uncertain than running a company during a pandemic. Like most people, worry about your own livelihood, family, friends, and loved ones and how you’ll cope during COVID-19 is at the top of your mind. But unlike others, you’ve got the added concern about your employees – both for their health and safety, as well as their financial health. While the government made some relief available in the earlier days of the pandemic such as forgivable loans like the Paycheck Protection Program (PPP) and Emergency Injury Disaster Loans (EIDL) one of the biggest benefits provided has to do with a little known tax provision to the tax law. This provision makes it possible to provide certain payments without tax during a terrorist attack or disaster, but if it weren’t for a certain interpretation of President Trump’s declaration in March 2020, this benefit wouldn’t exist for COVID-19.

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    Can I “Nominee” Income From a Schedule C to Another Return?

    I have a few physician clients who earn their income via Form 1099 and are perfect candidates for an S corporation. However, the hospital won’t issue the Form 1099 in the name/EIN of an S corporation. Is this an issue? Can I still report the income on the Form 1120S and report the Form 1099 on a Schedule C with a negative adjustment for the same amount and attach an explanation annually? Or is there any other way?

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    Year-End Tax Strategies for the Investor

    The end of the year is a time for holidays, family, and maybe overindulging at the dinner table. It can also be a time for substantial tax savings. There are many techniques a taxpayer can use to minimize their tax burden for the year. The key to many of them is acting before the calendar year comes to a close. Specifically, let’s examine tax strategies for the taxpayer with investments, such as stocks, bonds, and mutual funds. These strategies can help taxpayers lower taxes, keep more money in their pockets, and donate to their favorite charities.

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    More Cash Available for Employers Under Refundable Tax Credit

    As 2020 winds to a close, we have seen many beneficial programs provided by the Coronavirus Aid, Relief, and Economic Security Act (CARES Act) and the Families First Coronavirus Response Act (FFCRA). While most media coverage has focused on loans to employers such as PPP and EIDL, it is important to remember some of the lesser covered programs also included in the tax relief programs. In fact, eligible businesses may qualify to get cash back in some instances. The employee retention credit (ERC) under the CARES Act offers a refundable payroll tax credit for certain wages and health plan expenses paid by businesses during the economic hardship. However, many business owners have uncertainty as to how to qualify when they have also received a PPP loan. The paid sick leave and paid family medical leave credits also offer a refundable tax credit for qualifying wages and Medicare tax and health plan expenses. These refundable tax credits are stackable for maximum benefit when used correctly. Read on to discover how to qualify.

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    PPP Loan Forgiveness: Now What?

    It’s finally here! After much political wrangling, Congress and President Trump signed the Consolidated Appropriations Act, 2021 (HR 133) into law on December 27, 2020. Attached to this omnibus spending bill were a number of unrelated pieces of legislation, including the latest COVID-19 relief and stimulus measures. The law puts much needed cash in the hands of business owners and individuals alike, while Congress thumbs its collective nose at the IRS by including an override of the recent notice disallowing the deduction of expenses paid for using PPP funds. Several more key provisions in the new legislation’s Division N include process simplification and forgiveness for PPP borrowers, which will make life easier for everybody. To find out how to qualify for new rounds of stimulus, automatic forgiveness, and how to get both tax credits and free money, keep reading.

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    Why Can’t I Deduct PPP Payroll Expenses?

    Question: Given the recent passing of the stimulus law (CAA 2021) permitting a business to deduct payroll expenses paid with Paycheck Protection Program (PPP) funds, how does an S corporation or Partnership basis negatively impact this? I’m hearing that even though the law allows the deduction, some businesses will have suspended losses due to PPP funds. Which is true? Can a business deduct losses from PPP payroll or not?

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    Bob Dylan Shows How to Beat an Imminent Tax Increase

    Timing might be one of the oldest, most valuable tax strategies known. Essentially, a timing strategy allows a taxpayer to pay tax when rates are generally lower rather than when in a higher tax bracket or when facing increasing tax rates. Given this, 2020 may have been an optimal time to sell capital assets if tax rates rise under the new administration. President-elect Joe Biden has suggested taxing capital gains as ordinary income for high-income taxpayers (more than $400,000), as well as raising the top tax rate from 37% to 39.6%. Here’s how to cash in on the lower rates and, more importantly, when. While tax law changes seldom pass quickly, we often see changes made retroactive to the beginning of the year they are voted into law. Based on a recent story in The New York Times, Bob Dylan may have anticipated the increase when he sold the copyrights to his catalog of more than 600 songs for $300 million. Not to fret if you found yourself missing the beat of Dylan’s lead, there are many things a taxpayer can do to reduce capital gains tax, especially for self-created works of art. Here’s how.

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