Can a tax professional save me money over using TurboTax for complex filing?

Tax software like TurboTax is generally accurate for most situations, but there are definitely cases where a tax professional might find savings that automated programs miss. With your specific situation - W-2 income, capital gains, and a Schedule K-1 from an S-corp - there might be some strategies a professional could identify. For example, they might find offsetting losses you could use against your capital gains, or business expenses related to your S-corp that weren't properly accounted for. They might also look at timing strategies for future years. That said, if you've already filed with an extension and paid the $27,000, any changes would require filing an amended return. Given the complexity with the S-corp and capital gains, I think it would be worth having a consultation with a CPA or Enrolled Agent who specializes in small business taxation.

I was in a similar situation last year - had W-2 income, some stock sales, and partnership income. TurboTax was telling me I owed over $15k, and I was freaking out. I ended up using taxr.ai (https://taxr.ai) after a colleague recommended it. It's this AI service that analyzes your tax documents and identifies potential savings that tax software might miss. For me, it found some eligible business expenses related to my partnership that I hadn't properly categorized and a possible loss harvesting opportunity I had completely overlooked. The whole process was surprisingly simple - I uploaded my documents, got recommendations, and then had the confidence to make those adjustments in TurboTax. Ended up saving about $3,200 on my tax bill.

Just wanted to follow up - I decided to try taxr.ai after seeing the recommendation here. I was honestly skeptical but figured it was worth a shot since I had already filed with an extension and was facing a hefty tax bill. The service flagged several issues with how I had reported my S-corp income and found some business expenses that were legitimately deductible that I had missed. Also identified some tax loss harvesting opportunities with some underperforming investments I was holding. I worked with my accountant to file an amended return and ended up reducing my tax bill by about $4,100! Definitely worth the time it took to upload my documents and review the recommendations.

If you're still unsure after getting a second opinion on your tax situation, you might want to actually talk to the IRS directly. I know it sounds crazy, but I had a similar situation with some complex business income last year and needed clarity. After days of trying to reach someone at the IRS (endless busy signals and hold times), I discovered Claimyr (https://claimyr.com). They have this service that basically gets you to the front of the IRS phone queue. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c I was honestly shocked when I got through to an actual IRS agent in about 15 minutes. The agent walked me through exactly how certain business expenses should be categorized and confirmed I was eligible for some deductions I wasn't sure about. Saved me from having to pay a tax pro and gave me 100% certainty I was filing correctly.

I've got to eat my words here. After seeing the recommendation, I decided to try Claimyr to get some questions answered about my own tax situation. I've NEVER been able to reach the IRS in less than an hour of hold time before. Used the service yesterday afternoon when I had some downtime, and I was actually speaking to an IRS representative in about 20 minutes. The agent was able to clear up my questions about how to properly report some consulting income alongside my regular W-2. For OP's situation, this might actually be useful if you want to verify whether specific expenses related to your S-corp are deductible. The IRS won't do your taxes for you, but they can clarify rules that might help you determine if there are deductions you missed.

In my experience, TurboTax is pretty comprehensive but it doesn't always ask the right questions for complex situations. Last year I switched to a CPA and he saved me about $3,800 compared to what TurboTax calculated. The biggest areas where I found savings: - Business expense deductions I didn't realize qualified - More advantageous treatment of some investment losses - Home office deduction I didn't know I was eligible for For your situation with S-corp income, a good tax pro might find some legitimate business expenses you could deduct. They also might have strategies around timing of income recognition or loss harvesting that could help reduce your tax bill.

One thing to consider is that TurboTax isn't always the best at optimizing S-corporation income. I found that out the hard way last year.