At Hill Investment Group, we’ve found that when a few clients ask similar questions, many more likely share the same curiosity. To better serve you, we’ll periodically feature this “Hey Hill” segment in our newsletter, addressing common client questions and explaining our perspective. To submit questions for future newsletters, email us at service@hillinvestmentgroup.com.

Tax season always feels like a scramble. Are there things we (or you) can be doing throughout the year to make it easier – and smarter?

At Hill Investment Group, we believe taxes aren’t just a once-a-year concern. They’re a year-round opportunity. While most people only think about taxes in the spring, we’re building strategies into your plan every day—so you’re not just reacting in April, you’re planning ahead with purpose.

Markets move. Headlines shift. But one thing we can control is how efficiently your portfolio is managed from a tax perspective. It’s a key part of Taking the Long View, helping you keep more of what you earn—not just this year, but every year.

How We Build Tax Efficiency into Your Plan

• Strategic Asset Location – Some investments generate more taxes than others, and where you hold them matters. We structure your portfolio to keep tax-inefficient assets in tax-advantaged accounts, reducing unnecessary tax drag.
• Tax-Loss Harvesting – When the opportunity arises, we strategically offset gains with losses—lowering your taxable income without disrupting your investment strategy.
• ETF Investing – ETFs (Exchange-Traded Funds) allow investors to defer most, if not all, capital gains taxes until they sell, helping avoid surprise tax bills.
• Tax-Advantaged Accounts – From IRAs and Roth conversions to HSAs, we help you maximize the long-term tax benefits of these accounts.
• Charitable Giving Strategies – Tools like donor-advised funds, qualified charitable distributions (QCDs), and appreciated stock donations allow you to give while staying tax-smart.
• Estate & Gifting Strategies – Thoughtful wealth transfer planning helps minimize estate taxes and ensures your legacy is passed on efficiently.

Making Tax Season Easier

Beyond these long-term strategies, we make tax season seamless by preparing tax packets with key reports and details your CPA needs. Because we work closely with your tax team, we help ensure that your investment and tax strategies are always aligned.

If you have questions about how tax planning fits into your financial picture, we’re here to help.

Taking the Long View means thinking ahead—about taxes and beyond.

Happy tax season! I realize that’s probably an oxymoron for most people, but I have a confession: I like it. Suppose you’re obsessed with numbers and details like me. In that case, digging through diligent records in your file cabinet at home, ticking and tying every dollar of income, dividends, and interest, and accounting for every possible deduction is not a bad day, in my opinion (and it just might be how I spent my Sunday afternoon this weekend. There’s no more football, what else am I supposed to do?). And when the amount due matches precisely what you had calculated six months earlier… boy, does that feel good.

I know I’ve lost most people by now, but to anyone who has read this far, I reward you with some last-minute reminders as you gather up your tax documents to send to your CPAs (or for the brave, as you fire up your preferred tax preparation software and do it yourself!).

1. You probably hear this every year, but there is still time to make a 2023 contribution to an IRA or Roth IRA! You have until the date that you file your 2023 taxes to contribute. We generally prefer the Roth IRA if you’re below the gross income limits for 2023 (single filers: $138,000 / joint filers: $218,000). If you’re above the income limits, you can still choose to make a Backdoor Roth contribution. This would involve making a nondeductible 2023 IRA contribution and then immediately converting that amount to Roth. These rules can vary from person to person, so please reach out to us if you’d like to discuss this!
2. Don’t forget about Roth IRAs for your kids! The only requirement to contribute to a Roth IRA is “earned” income. Babysitting, mowing lawns, washing cars…it all counts, even if no W-2 or 1099 is issued. There is no age limit as long as there is real earned income. I emphasize real because doing chores around the house or babysitting for siblings one night doesn’t count. As a general rule of thumb, the Roth IRA is fair game if you have your kids file a tax return for their income. Each child is limited to the higher of $6,500 or their earned income (so if they earned $1,000, the limit is $1,000). Another great benefit is that they don’t have to use their money. You can make the contribution on their behalf.
3.   If you have a high-deductible health plan with a Health Savings Account, ensure you and your employer contributions have hit the 2023 maximum ($3,850 for self-only coverage and $7,750 for family coverage). Add an extra $1,000 to that if you’re over 50. You have until your tax filing date to top off those contributions with after-tax funds.
4.  If you live in a state with no state income tax (where two of our three Hill offices reside – sorry, St. Louis), you will likely get a deduction for sales taxes you paid in 2023. You could collect every receipt and total the sales tax on every item you purchased in 2023 (and I would not judge you), or you can do what most people do and take the IRS’s estimated amount. Most people don’t realize, however, that you can also add sales tax from significant purchases on top of the estimated amount. If you bought a car, boat, or Super Bowl tickets (really anything that made you wince when you swiped the credit card), don’t forget to tell your tax preparer! Unfortunately, state and local taxes are limited to a total deduction of $10,000, so there’s a good chance your property taxes already exceed that limited amount anyway.
5.  If you have self-employment income (as reported on Schedule C), don’t forget to make a SEP-IRA contribution. The limit is based on your amount of self-employment income, but the contribution itself will also count as an “expense” against your self-employment income. Your tax preparer can tell you how much you can contribute to a SEP IRA.
6. Lastly, here’s a list of a few pesky little forms that can be missed. Don’t forget to send these to your tax preparer!

• Form 5498: If you have an IRA, you have a 5498! This is an informational form that tracks contributions and distributions from IRAs and Roth IRAs. You can file your taxes without it, but giving these to your CPA will ensure that your IRA cost basis information is kept accurate year over year, especially if you’ve ever made nondeductible (after-tax) IRA contributions.
• Form 1099-SA: If you took money out of a Health Savings Account in 2023, this form will report that amount. A copy of this is also sent to the IRS, so you might get a letter in the mail if you forget it.
• Qualified Charitable Distributions (QCD): If you sent any portion of a required minimum IRA distribution directly to a 501c(3)charity, your form 1099-R will NOT specify that. It’s the tax preparer’s responsibility to note any QCDs. If HIG facilitated a QCD for you in 2023, you have nothing to worry about. We’ll let your tax preparer know.

And if you’ve made it THIS far, I applaud you and thank you for sticking it out. I leave you with a quote:  “Of life’s two certainties, there is only one where you will be granted an extension.” –Anonymous.

This information is educational and does not intend to make an offer for the sale of any specific securities, investments, strategies, or tax advice.  Investments involve risk and, past performance is not indicative of future performance. Return will be reduced by advisory fees and any other expenses incurred in the management of a client’s account. Consult with a qualified financial adviser or CPA before implementing any investment or tax strategy.

Client Question: 

Why didn’t you tell me how simple you were going to make my tax life?

HIG Reply: 

We like good surprises! Because each client’s tax situation is unique, the time and dollars saved are challenging to quantify in advance. No matter your situation, we are confident your tax experience will likely improve, whether your tax bill this year goes up or down.

You may be asking yourself, “how can I save more on taxes?”. Whether you are wondering about this year or next, if you’re a client, you already know you have a team working on it. We provide a spectrum of services to minimize your tax bill, in addition to guidance throughout the year and regular evaluation of potential tax law changes. In other words, you don’t have to worry that you’re leaving money on the table – we’re already working with you and your tax team to avoid that. If you want to learn more about how we see tax management schedule a complimentary call with us – we’d love to chat!

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