Tax season for families with complex financial structures often requires more than gathering documents. It typically calls for strategic coordination. While April 15th may be months away, we believe the conversations you have with your tax advisors now can meaningfully impact your filing accuracy, compliance, and overall tax planning outcomes.
What’s New for Tax Year 2025
The IRS has adjusted key figures for 2025 that may affect your situation. Standard deductions increased to $15,750 for single filers and $31,500 for married filing jointly. For seniors aged 65 and older, there is an additional deduction of $6,000 ($12,000 for married couples).[1]
However, given the complexity of most high-net-worth tax situations (multiple income streams, investment activities, trust distributions) itemizing typically remains the more advantageous approach. Note that the cap on state and local taxes (SALT) that itemizers may deduct went from $10,000 to $40,000 for 2025-2029. Estate and gift tax exemptions also saw inflationary adjustments, relevant for families engaging in wealth transfer strategies throughout the year.
More significantly, IRS enforcement efforts have intensified around high-income filers, particularly regarding partnership interests, digital asset transactions, and international holdings. Documentation standards have effectively tightened, making thorough preparation more critical than in previous years.
The Coordination Challenge
Families with complex financial structures typically work with multiple advisors: a wealth manager overseeing investments, a CPA handling tax preparation, and estate attorney structuring trusts, and if applicable, business attorneys advising on operating companies. Each professional generally operates within their domain, yet tax filing requires information that crosses these boundaries.
Common coordination gaps may create unnecessary complications. Your CPA may not know about the charitable donations your wealth advisor facilitated through a donor-advised fund. Trust distributions coordinated by your estate attorney might not be communicated to your tax preparer until K-1s arrive, which is often after your desired filing timeline. Investment decisions made for portfolio optimizations may have created wash sale issues or short-term gains that conflict with your overall tax strategy.
In our experience, the families who navigate tax season most efficiently tend to be those who proactively facilitate information flow between their professional team rather than assuming it happens automatically.
Essential Conversations to Have with Your Tax Advisor
Rather than simply delivering documents, we suggest you approach your CPA relationship as a strategic collaboration. These conversations should happen well before filing season peaks:
Income Complexity and Documentation Timing: Discuss the expected timeline for receiving K-1s from partnerships, LLCs, or S-Corporations in which you hold interests. If you have investments in private equity, real estate partnerships, or operating businesses, these schedules typically dictate your filing timeline. Some partnerships don’t issue K-1s until mid-March, and if your CPA isn’t expecting them, they may file prematurely without crucial income information.
Similarly, if you have trust distributions, rental properties, or foreign income, your CPA may want advance notice to ensure proper reporting forms and schedules are prepared.
Investment Activity and Tax Strategy Alignment: Your investment transactions throughout 2025 have tax implications that your CPA should understand in context. Did BSW harvest losses to offset gains? Were there significant Roth conversions? Did you exercise stock options or receive restricted stock that vested?
Charitable Contributions and Documentation: For families making substantial charitable contributions, particularly through donor-advised funds, private foundations, or gifts of appreciated securities, documentation requirements are precise. Cash contributions over $250 require written acknowledgement from the charity. Non-cash contributions over $500 require Form 8283, and those over $5,000 typically require qualified appraisals.
For BSW clients, if you donated appreciated stock, your BSW advisor has the transaction records, but your CPA needs the cost basis information and confirmation of fair market value on the donation date.
Business Interests and Expense Documentation: If you own an operating business or have significant self-employment income, your bookkeeper or business accountant may handle day-to-day accounting, but your CPA needs to understand how business income flows through to your personal return. Home office expenses, vehicle usage, health insurance premiums paid through your business, and retirement plan contributions all require coordination between your business accounting and personal tax preparation.
What Your CPA Needs from You
Beyond the standard income documents, complex tax preparation requires comprehensive documentation that may not be immediately obvious. For a helpful summary, click here:
Tax Season Preparation Checklist for 2026
In our opinion, your tax preparation meeting shouldn’t simply be a document handoff. Consider asking your CPA:
- Based on this year’s filing, what estimated tax payment adjustments should we make for 2026?
- Are there any positions on this return that have higher audit risk, and how have we documented them?
- What planning opportunities exist for the remainder of 2026 based on what you’re seeing in this return?
- Should we consider any entity structure changes for my business interests?
- Are there any state tax considerations I should be aware of given my income sources?
These questions may help transform tax preparation from a compliance exercise into strategic planning.
Looking Ahead
We believe the most effective approach to tax season is treating it as a year-round coordination effort rather than an annual scramble. As you gather documentation for 2025, consider implementing systems that make the next year more efficient.
Your CPA brings specialized expertise to tax preparation and compliance, and you play an important role in helping connect the pieces of your overall financial picture. In our experience, families who experience smoother tax seasons are those who recognize this role and proactively facilitate the information flow that enables their advisors to do their best work.
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Disclosures:
This blog is created and authored by BSW Wealth Partners, Inc., a Public Benefit Corporation (“BSW”) and is published and provided for educational and informational purposes only. The opinions expressed in the blog are our opinions and should not be regarded as a description of services provided by BSW or considered investment, legal or accounting advice. Certain information sited is from third-party sources and while we believe the information to be accurate and true to the best of our knowledge, we cannot guarantee its accuracy as there may be certain unknown omissions, errors, or mistakes. Use of third-party information, including links, is in no way an endorsement by BSW. The views reflected in the blog are subject to change at any time without notice.
This article was published on February 13, 2026, and reflects tax law as of January 2025. Tax laws, regulations, and interpretations are subject to change, which could materially impact the information presented. Readers should verify current tax law before relying on any information contained herein.
The observations about client experiences and tax preparation outcomes are based on BSW’s experience working with clients and do not constitute a guarantee of results. Individual outcomes vary based on personal circumstances, quality of documentation, advisor coordination, and other factors. Past results do not guarantee future outcomes.
Nothing on this blog constitutes investment advice, performance data, or any recommendation that any security, portfolio of securities, investment product or investment strategy is suitable for any specific person. Please remember that past performance may not be indicative of future results. Different types of investments involve varying degrees of risk, and there can be no assurance that the future performance of any specific investment, investment strategy, or product (including the investments and/or investment strategies recommended or undertaken by BSW), or any non-investment related content, made reference to directly or indirectly in this blog post will be profitable, equal any corresponding indicated historical performance level(s), be suitable for your portfolio or individual situation, or prove successful. Not all BSW clients will have the same experience within their portfolio(s) and certain topics discussed in this blog may not apply to all clients or investors. Due to various factors, including changing market conditions and/or applicable laws, the content may no longer be reflective of current opinions or positions. Moreover, you should not assume that any discussion or information contained in this blog serves as the receipt of, or as a substitute for, personalized investment advice from BSW. To the extent that a reader has any questions regarding the applicability of any specific issue discussed above to his/her individual situation, he/she is encouraged to consult with the professional advisor of his/her choosing. BSW is neither a law firm nor a certified public accounting firm and no portion of the blog content should be construed as legal or accounting advice. A copy of BSW’s current written disclosure statement discussing our advisory services and fees is available upon request.
[1] The figures presented reflect 2025 tax law as understood at the time of publication. Tax planning decisions should be made in consultation with qualified tax professionals who can evaluate your specific circumstances. We recommend confirming current tax law with your tax advisor before making any decisions.
