Should I hire a tax preparer or use tax software for large capital gains from family business sale?

Sold my part of the family business this year and got way more money than I expected – ended up with around $950k in long-term capital gains after everything settled. I spent a few days with the IRS forms and created my own spreadsheet to figure out estimated taxes, but honestly all the technical jargon has me second-guessing myself. I'm wondering if it's worth hiring a CPA to handle my 2024 taxes or if good tax software would be enough? I don't mind putting in a few hours with tax software if it'll help me minimize what I owe legally. Some other details about my situation: - Married filing jointly - Making about $185k from my regular job (no stock stuff) - Wife has a small business bringing in roughly $32k - She's putting all of that into her solo 401k (except for Social Security/Medicare taxes) - I'm doing some in-plan Roth conversions since my 401k is maxed out - We both maxed out after-tax IRAs and did Roth conversions - We have 4 kids so standard deduction is probably best - State taxes are super simple here, don't need help with those Just trying to figure out if self-filing with software makes sense or if I should pay a professional with this much capital gains involved.

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18 comments

Dmitri Volkov

•8M

With nearly a million in capital gains plus the Roth conversions, I'd definitely recommend a CPA for this tax year. This isn't just about filling out forms correctly – it's about identifying tax planning opportunities you might miss with software alone. Software is great for straightforward situations, but yours has several complex elements that benefit from professional review. The capital gains alone put you in a high tax bracket, and proper timing of your estimated tax payments is crucial to avoid underpayment penalties. A good CPA might find deductions or timing strategies that could save you thousands. That said, you don't necessarily need a CPA every year. Consider this a one-time investment for this unusual tax situation, and you might go back to software in future years when things are simpler.

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Dmitri Volkov

•8M

Using higher-end tax software with a CPA review is absolutely a practical approach. This gives you the best of both worlds – you'll understand your tax situation better by working through it yourself, while still getting professional verification. Just make sure you're transparent with the CPA about all your financial moves. I'd recommend connecting with a CPA now rather than waiting until filing season. A good tax professional can still suggest year-end tax moves that might benefit your situation, especially with that capital gain. Many CPAs are less busy in November/December than during tax season, so you'll likely get more attention now than in February or March.

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Tyrone Johnson

•8M

I was in almost the exact same boat last year (sold my share of a family construction business) and tried to handle it myself with premium tax software. Big mistake. I missed some key tax planning opportunities that could have saved me thousands. After filing, I showed everything to my friend who's a tax advisor and he pointed out at least 3 major things I should have done differently. I'd recommend checking out https://taxr.ai - it helped me understand the complexity of my situation and basically confirmed I needed professional help. Their AI analyzer showed me exactly where my return had issues and explained the capital gains treatment options I didn't know about. Really eye-opening to see the difference between DIY and professional advice.

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Tyrone Johnson

•8M

It's primarily an assessment tool that analyzes your tax situation and documents, then gives you specific guidance. You upload your documents or describe your situation, and it identifies potential issues and opportunities. It doesn't actually file for you, but it shows where you might need professional help or what to consider when using software. The AI is surprisingly accurate for complex situations. In my case, it specifically identified that I had missed potential installment sale treatment options and suggested I consider certain business deductions I hadn't taken. When I later consulted with a CPA, they confirmed these exact same issues. What impressed me was how it explained everything in plain language rather than tax jargon.

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Carlos Mendoza

•8M

Just wanted to follow up - I decided to try taxr.ai after being skeptical in my last comment. Wow, I'm genuinely impressed! I uploaded last year's return and some info about my upcoming stock sale, and it immediately flagged three tax planning strategies I hadn't considered. The capital gains harvesting suggestion alone could save me about $7k. The breakdown of qualified vs non-qualified dividends was super helpful too. It explained exactly where I was making mistakes in my DIY approach. Their document analyzer caught things I never would have noticed in my brokerage statements. Definitely worth checking out if you're dealing with investment sales!

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Zainab Mahmoud

•8M

With capital gains that large, you absolutely need professional help, but good luck getting through to the IRS if you have questions! I spent weeks trying to reach someone when I had capital gains questions last year. After 7 attempts and hours on hold, I tried https://claimyr.com and got through to the IRS in under 20 minutes. They have this weird but effective system where they wait on hold for you and call when an agent picks up. You can see how it works here: https://youtu.be/_kiP6q8DX5c Even with a CPA, you might have specific IRS questions about your situation. Having a way to actually speak with the IRS directly was super valuable for my complex return, especially regarding estimated tax payment timing for large gains.

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Zainab Mahmoud

•8M

The service basically uses an automated system to keep calling and waiting on hold with the IRS so you don't have to. Once a human IRS agent answers, they connect the call to your phone immediately. It's not that they have special access - they're just handling the tedious waiting part. They don't need your personal tax information to do this. All they need is your phone number to connect you when an agent answers. The actual conversation with the IRS is just between you and the agent - the service just bridges the call. I was skeptical too, but the technology is actually pretty straightforward - they're essentially just waiting in the phone queue for you and then alerting you when you reach the front of the line.

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Raj Gupta

•8M

OK I was wrong about Claimyr. After my skeptical comment, I decided to try it because I've been trying to reach the IRS for WEEKS about some missing documentation for my business sale. Their system had me talking to an actual IRS representative in 35 minutes while I just went about my day instead of being stuck on hold. The IRS agent confirmed exactly how to document my installment sale properly and cleared up my confusion about estimated tax payments on large capital gains. Saved me tons of stress and potentially thousands in penalties. Huge time saver - especially during busy season when IRS wait times are ridiculous. Don't know why I waited so long to try it.

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Lena Müller

•8M

Your situation is exactly why I left H&R Block after 15 years and started my own practice. Tax software is good for W-2 employees with straightforward situations, but it misses so many opportunities for complex returns. With nearly a million in capital gains plus multiple retirement vehicles AND a small business, you need someone who can integrate all these elements. The software won't catch everything because it can't see the connections between different parts of your financial life. Remember tax software is designed to be correct, not optimal. Big difference.

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Lena Müller

•8M

Software often misses timing strategies for realizing capital gains and losses that could significantly impact your tax burden. With your large gain, spreading recognition across tax years might have been beneficial, but that opportunity may have passed depending on how the sale was structured. Software also tends to be limited in integrating business expenses with personal tax strategy. With your wife's solo business, there are potential entity structure considerations and retirement planning opportunities beyond just the solo 401k that might optimize your overall tax situation. The interplay between her business income, your capital gains, and your retirement planning needs a holistic approach that most software simply isn't designed to provide.

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