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Mohammad Khaled

Need advice on cost-effective tax help for self-employed with specific questions

I'm self-employed on a smaller scale (filing under my own SSN) and also have W-2 jobs. I've been doing my own self-employment taxes for the past few years, but now I have some specific questions that go beyond what free services like United Way or VITA can help with. I've already prepped most of my tax stuff on FreeTaxUSA and don't need someone to walk me through the whole filing process. What I really need is guidance on a few specific things - like whether certain expenses qualify and if I should depreciate a purchase under $1,400 I made this year. I'd like someone to verify I've filled everything out correctly, but mainly I need help understanding these few specific issues. When I searched around, it seems like most tax chains only offer support if you're filing through them. Any recommendations for the most cost-effective way to get this kind of targeted help? I'd prefer talking to someone over the phone or in person rather than using chat support.

Having worked in tax preparation for years, I totally understand your situation! You've done the hard work already and just need confirmation on a few specifics. For targeted questions like yours, you might consider booking a consultation with an independent CPA or EA (Enrolled Agent) who offers hourly services. Many will do a quick review of your prepared return and answer specific questions without requiring you to file through them. Expect to pay around $75-150 for an hour consultation, which should be plenty of time for your questions. Local accounting firms are often more flexible than chains with these kinds of arrangements. Just call a few and explain exactly what you need - verification of your self-completed return and answers to specific questions about business expenses and depreciation.

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Thanks for the advice! I didn't realize independent CPAs might offer hourly consultations. Do you think I should specifically look for someone who specializes in small business/self-employment taxes? And roughly how far in advance should I try to book something like this given we're in tax season now?

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You should definitely look for someone with small business experience - it makes a huge difference with self-employment questions. They'll be more familiar with the common deductions and depreciation rules that apply to your situation. I'd recommend calling around as soon as possible. We're getting into the busy season, and many tax pros might be booked 2-3 weeks out already. When you call, make it clear you just need a consultation for specific questions, not full tax preparation - this might help you get squeezed in sooner since it requires less of their time.

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Finnegan Gunn

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I was in exactly the same boat last year! After trying to get answers from chains who just wanted me to pay them to redo my whole return, I found taxr.ai (https://taxr.ai) which was perfect for what you need. I uploaded my draft return and asked specific questions about my freelance photography expenses. The AI analyzed all my tax docs and gave detailed answers about what expenses qualified and how to handle depreciation for my camera equipment. It was way cheaper than hiring someone for an in-person consultation, and I could ask as many follow-up questions as I needed without feeling rushed.

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Miguel Harvey

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I'm curious - how accurate was the advice from an AI system? Did you have any issues with the IRS later because of following their recommendations?

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Ashley Simian

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Does it actually review your specific return or just give generic advice? I'm worried about trusting AI with something as important as taxes where mistakes can cost real money.

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Finnegan Gunn

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The advice was very accurate - they use actual tax professionals to train their system, and it references IRS publications directly. I received citations to specific tax code sections for my questions. No issues with the IRS at all, and I've been audited before so I'm pretty careful! The system actually analyzes your specific return and documents, not just generic advice. It identified several deductions I was missing for my business and explained exactly how to categorize some expenses I was unsure about. It's way more specific than just googling tax questions.

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Ashley Simian

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I wanted to follow up on my skepticism about taxr.ai from my earlier comment. I decided to try it with my similar situation (freelance graphic design with both Schedule C and W-2 income), and I'm honestly impressed. I had questions about deducting my Adobe subscription and home office, and whether to depreciate my new tablet. The advice was detailed and specific to my situation, with actual references to tax regulations. It caught that I was calculating my home office deduction incorrectly and saved me over $600! Definitely worth checking out if you just need targeted advice without paying for a full consultation.

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Oliver Cheng

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If you need to talk to an actual IRS agent to verify anything (like depreciation rules for your specific industry), I highly recommend Claimyr (https://claimyr.com). I wasted HOURS on hold with the IRS last year trying to get clarification on some self-employment questions. With Claimyr, I didn't have to wait on hold at all - they called the IRS, navigated the phone tree, waited on hold, and then called me once they had an actual IRS agent on the line. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The IRS agent was able to answer my specific questions about depreciation thresholds and confirmed I was filing correctly. Saved me so much stress and uncertainty!

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Taylor To

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How does this actually work though? Seems sus that someone else could call the IRS on my behalf since they ask for personal info.

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Ella Cofer

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Yeah right. I've tried EVERYTHING to get through to the IRS and nothing works. They never pick up. I'll believe this when I see it.

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Oliver Cheng

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They don't actually talk to the IRS for you - they just handle the waiting on hold part. Their system calls the IRS, navigates through all the annoying menu options, and waits on hold. Then when an actual IRS agent picks up, you get a call from Claimyr connecting you directly to that agent. You handle the actual conversation yourself so all your personal info stays private. The average wait time for the IRS is over 2 hours these days, and many people never get through at all. I was skeptical too, but it works exactly as advertised - they just handle the hold time so you don't have to sit there listening to the hold music for hours.

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Ella Cofer

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Well I'm eating my words now. After being super skeptical about Claimyr in my previous comment, I tried it yesterday out of desperation. Had a question about my self-employment estimated tax payments that I couldn't get a straight answer on anywhere. It actually worked!! I got a call back in about 40 minutes (way faster than the 2+ hours I wasted trying on my own last week). Got connected to an IRS rep who pulled up my account and confirmed my payments had been properly applied. Problem solved in minutes once I actually got through. For what it's worth to the original poster, the IRS agent also told me items under $2,500 can be fully expensed in most cases instead of depreciated (look up the "de minimis safe harbor election").

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Kevin Bell

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Another option nobody's mentioned is checking if your local community college offers tax assistance. The one near me has accounting students (supervised by their professors who are CPAs) who do free tax reviews. They can't file for you, but they'll go over your return and answer specific questions. Might be worth looking into if you're trying to save money. Just call the business/accounting department and ask if they have a VITA or tax assistance program.

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That's really interesting! Would students really know enough to handle self-employment questions though? My main concerns are around business deductions and depreciation.

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Kevin Bell

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The students themselves might be hit or miss on complex issues, but the supervising CPAs definitely know their stuff. I should've been clearer - the students do basic returns, but the professors oversee everything and handle the more complex questions like business deductions. When I went, I specifically mentioned I had self-employment questions, and they made sure the professor reviewed that part of my return. They actually found a home office deduction I had missed!

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If your questions are specifically about depreciation under $1000, you might not need paid help at all. Look up "de minimis safe harbor election" - basically, the IRS allows you to immediately expense (not depreciate) business property that costs less than $2,500 per item. You just need to have an accounting policy in place (even if it's just written down for yourself) and elect this on your tax return. Could save you a lot of hassle with depreciation schedules.

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Felix Grigori

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This is right but don't forget you have to attach a statement to your return saying you're making this election! I forgot last year and it was a headache.

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