Year-End Tax Checklist for Investors with Complex Portfolios

📅 Updated for 2025

If you’ve got RSUs, ESPPs, crypto, or multiple brokerage accounts, tax season isn’t something you should only think about in April. Some of the best opportunities to reduce your tax bill and avoid costly mistakes come before the year ends.

Here’s a year-end checklist tailored for investors with complex portfolios.

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✅ 1. Harvest Capital Losses (Intentionally)

What it is: Selling losing investments to offset capital gains.

Why it matters:

• Capital losses offset capital gains dollar-for-dollar
• You can deduct up to $3,000 of net losses against ordinary income
• Any unused losses carry forward to future years
  

Action:

• Review each taxable brokerage and crypto wallet for unrealized losses
• Avoid the wash sale rule (sell and repurchase substantially identical assets within 30 days)
• Note: Crypto currently isn’t subject to wash sales (as of 2025)
  

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✅ 2. Take Capital Gains If You’re in a Low Bracket

If you’re temporarily in a lower tax bracket (e.g., due to a job break or sabbatical), this might be your golden opportunity.

Why it matters:

• The 0% long-term capital gains rate applies if your taxable income is under $94,050 (married filing jointly in 2025)

Action:

• Check your projected income
• Consider realizing long-term gains on purpose. You might owe zero federal tax
  

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✅ 3. Maximize Tax-Deferred Contributions

There are a lot of ways to save on your taxes now and in the future:

• 401(k) limit in 2025: $23,000 (+$7,500 catch-up if age 50+)
• HSA limit: $4,300 individual / $8,600 family
• Traditional IRA phaseouts: Check if you’re eligible based on income and plan access
  

Action:

• Increase final pay period deferrals to max out accounts
• Use bonuses to top off HSA or IRA contributions
• Consider backdoor Roth contributions if your income is too high for direct Roth IRA eligibility
  

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✅ 4. Get Your RSUs, ESPPs, and Stock Sales in Order

Equity compensation is one of the most common sources of tax confusion.

Checklist:

• 🗂️ Save your vesting schedules and brokerage statements
• 🧾 Identify cost basis and sale dates for every stock you sold
• 📅 Review any shares sold for tax withholding, those may not fully cover your tax bill
• 📉 If your company stock has dropped in value, consider selling before year-end to capture losses
  

Pro Tip:
Print and save Form 3922 (ESPP) or Form 3921 (ISO) if you received them. Your CPA will thank you.

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✅ 5. Calculate and Withhold for Crypto Taxes

Crypto transactions, even swaps, are taxable.

Checklist:

• Download complete transaction history from each exchange or wallet
• Run a gain/loss report with a crypto tax tool (like CoinLedger, Koinly, or CoinTracker)
• If you earned staking, interest, or airdrops: expect ordinary income, not just capital gains

Warning:

• The IRS is enforcing crypto reporting more aggressively every year, and the rules always seem to be changing.  Make sure you stay up to date.
  

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✅ 6. Check Estimated Payments or Withholding

With complex investments, you’re more likely to owe at tax time unless you prepay.

Action:

• Use a tax projection tool or hire a CPA to estimate your total tax liability
• Check how much you’ve already withheld.

Avoid penalties by ensuring you’ve paid:

• 90% of your current year tax or
• 100–110% of last year’s tax (safe harbor)
  

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✅ 7. Gift or Donate Strategically

You can lower your tax bill and do some good.

Options:

• Gift appreciated stock to charity (no capital gains tax for you, full deduction for FMV)
• If you get distributions from an IRA consider donating straight to a charity with a qualified charitable distribution to avoid the .5% floor on charitable deductions (starts in 2026).  Donating this way also lowers your AGI, and you don’t have to itemize to get the benefit. 

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✅ 8. Talk to a Tax Pro Before December 31st

If your portfolio is even moderately complex, don’t wait until March to find a tax preparer. By then, the best ones are booked—or scrambling.

A good CPA can help you:

• Time trades or equity sales for tax efficiency
• Work with your financial advisor to coordinate your investments and taxes
• Plan AMT strategies (especially for ISO holders)
• Review cost basis and withholding
• Avoid IRS mismatches on 1099s
  

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⚡ Final Thoughts: Taxes Aren’t Just for April

If your portfolio has crypto, RSUs, ESPPs, multiple brokerages, or just a lot of moving parts, year-end is the best time to take control. Don’t let surprise tax bills catch you off guard, or leave easy tax savings on the table.

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📞 Want Help? Let’s Talk

If you’re feeling overwhelmed by stock options, RSUs, or crypto in your portfolio, you’re not alone. I specialize in tax planning for individuals with complex compensation, especially in tech, startups, and small business ownership.

At Wise.CPA, I offer flat-fee, paperless, and fully remote tax services, built around clarity and transparency. Whether you’re planning ahead or need help sorting out past transactions, I’m here to guide you.

📩 Contact me today to schedule a consultation or learn more about how I can help