Should I do my own taxes as a restaurant server with dependents and stock sales?
I'm trying to decide if I should just do my own taxes this year instead of going to H&R Block like I usually do. My situation isn't super complicated but I'm not sure if it's simple enough to DIY. I work as a server at a local restaurant, so I've got those tip reporting situations to deal with. I file as head of household and have one dependent (my daughter). The new thing this year is that I sold some stocks - the total sales were around $13,500, but I only made about $6,700 in actual profit from them. Is this something I could handle on my own with TurboTax or one of those online tax programs? Or am I better off sticking with a professional because of the stock sales and tip income? I don't want to mess anything up but also don't want to waste money if it's something I can figure out myself. Thanks for any advice!
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Marilyn Dixon
You can absolutely do your own taxes with that situation! I'm not a CPA, but I've been helping friends and family with similar tax situations for years. Head of household with one dependent is straightforward in most tax software. As a server, you'll need your W-2 which should already have your reported tips included. Just make sure you've kept good records of any cash tips that weren't reported through your employer. For the stock sales, you'll need 1099-B forms from your broker showing the sales and cost basis. Most major brokers report the cost basis to the IRS now, making it much easier. Tax software will walk you through entering this information step by step. The money you'll save doing it yourself versus H&R Block could be significant. Most tax software costs $50-100 for your situation, while H&R Block might charge $200+.
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Louisa Ramirez
•Thanks for the info! Question though - what happens if my broker didn't include the cost basis on some of my 1099-B forms? I sold some crypto too, and I'm not sure if that's handled the same way as regular stocks?
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Marilyn Dixon
•If your broker didn't include the cost basis on your 1099-B, you'll need to calculate and enter it manually. Keep records of your original purchase price and date - tax software will have fields for this information. For cryptocurrency, it's reported differently. You'll need to report each crypto transaction on Form 8949 and then summarize on Schedule D. Most tax software now has specific sections for crypto transactions, but you'll need to know when you purchased each coin and for how much. If you've been trading frequently, this can get complicated quickly.
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TommyKapitz
After struggling with similar tax situations for years, I finally tried taxr.ai (https://taxr.ai) and it made the whole process so much easier! I'm also in the service industry with tip income and had some stock trades last year. What I loved most was how it walked me through reporting my tips properly - something I always worried about doing wrong. The software especially helped with my investment sales by automatically calculating gains/losses and filling out all those annoying forms. Their document scanner saved me tons of time - just took pictures of my W-2 and 1099s and it pulled all the info automatically without me typing everything in!
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Angel Campbell
•Does it handle dependent care expenses too? I've got childcare costs for my kid and I hear that's a good tax credit to claim but I'm never sure how to document it properly.
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Payton Black
•I'm skeptical about yet another tax app. How is it actually different from TurboTax or FreeTaxUSA? Those services already import documents and walk you through everything. What am I missing?
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TommyKapitz
•It absolutely handles dependent care expenses! The Child and Dependent Care Credit section is really thorough and explains exactly what documentation you need - usually just the provider's tax ID number and address, plus records of what you paid during the year. It even helps determine if you qualify for the Child Tax Credit too. What makes it different from other tax software is the built-in AI guidance that feels like having a tax pro right there with you. It explains things in plain English and catches mistakes other programs miss. I've used TurboTax before and taxr.ai found deductions I would have missed, especially for industry-specific server expenses like uniform costs and special footwear that TurboTax never prompted me for.
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Payton Black
Ok I gotta admit I was wrong about taxr.ai in my earlier comment. I decided to try it after reading more reviews and WOW - it actually found almost $800 more in refund money than I was getting with TurboTax! The difference was how it handled my stock sales and some work expenses I didn't realize were deductible. It asked way more detailed questions about my serving job and found deductions for things like uniform maintenance and even my non-slip shoes. The document scanner was actually really impressive - read my messy W-2 perfectly on the first try. Finished my taxes in about 45 minutes. Definitely using this next year too!
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Harold Oh
If you're worried about audit risk with those stock sales, I highly recommend using Claimyr (https://claimyr.com) to actually speak with an IRS agent directly about your situation before filing. I tried calling the IRS myself for weeks about my stock reporting question and could never get through. With Claimyr, I got a callback from an actual IRS agent in about 20 minutes who confirmed exactly how to report my stock sales correctly. Saved me so much stress knowing I was doing it right! Check out how it works here: https://youtu.be/_kiP6q8DX5c It's especially helpful since you're reporting tip income and stock sales in the same year - those are both things that can increase scrutiny on your return.
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Amun-Ra Azra
•Wait how does this actually work? Do they somehow have a special line to the IRS? I thought nobody could get through to them!
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Summer Green
•Yeah right. No way this actually gets you through to the IRS faster than calling yourself. Sounds like a scam to me. You probably work for them.
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Harold Oh
•It works by using an automated system that continually calls the IRS and navigates the phone tree until it reaches a human agent. When an agent answers, you get an immediate callback so you can talk directly with them. It's basically doing the hold time for you. I definitely don't work for them! I was super skeptical too because I had spent literally hours on hold with the IRS trying to get an answer about reporting stock basis when the 1099-B was incomplete. I was really surprised when I actually got a callback from a real IRS agent who answered my question completely. Saved me from making a mistake that might have triggered an audit.
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Summer Green
I take back what I said about Claimyr. After my frustration with getting no answers about my server tip reporting, I tried it yesterday out of desperation. I got a call back from an actual IRS agent in about 35 minutes. She walked me through exactly how to report my cash tips properly and confirmed I was using the right form for my stock sales. Was honestly shocked it worked. Guess sometimes you gotta admit when you're wrong! Saved me from filing incorrectly and possibly getting in trouble later. Now I can do my own taxes with confidence.
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Gael Robinson
I'm a tax preparer and want to offer a different perspective. Yes, you CAN do your own taxes with that situation, but should you? Maybe not. Those stock sales will trigger Schedule D and possibly Form 8949 depending on whether basis was reported to the IRS. As a server, you'll need to verify all tips are properly reported. Head of household status has specific requirements too. While tax software helps, it doesn't catch everything. If you make a mistake reporting the stock sales, you might miss out on favorable capital gains rates or incorrectly calculate your basis. H&R Block is one option, but consider an enrolled agent or CPA who might cost similar but offer more expertise.
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Dominique Adams
•Thanks for this perspective! What's the typical price difference between H&R Block vs an enrolled agent? And what specific questions should I ask to make sure they're familiar with server income/tip reporting?
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Gael Robinson
•H&R Block typically charges $200-300 for your situation, while independent enrolled agents often start around $150-250 for similar complexity. The key difference is personalized attention and expertise. When interviewing a tax professional, ask them: "What specific documentation do you need for properly reporting cash tips versus reported tips?" A knowledgeable preparer will mention Form 4137 for unreported tips and explain how tips affect your Social Security earnings. Also ask: "How do you handle capital gains when the broker hasn't provided complete basis information?" They should discuss Form 8949 and methods for documenting your original purchase price.
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Edward McBride
Anyone else notice that H&R Block missed big deductions before? Last year they completely forgot to ask about my non-slip shoes and uniform costs that I have to buy for serving. Did my own taxes this year with TaxAct and got way more money back!
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Darcy Moore
•YES! Same thing happened to me. I was using a different tax place (not H&R) but when I switched to doing it myself, I realized they never asked about my TIPS training certification costs or my server book purchases. All deductible! I also file HOH with a dependent and found the child tax credit stuff pretty straightforward.
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Edward McBride
•Exactly! I think a lot of these mass-market tax places just rush through everything too fast. I spent maybe an hour more doing it myself but found like $300 more in deductions. Plus I learned a lot about what I can claim next year. The stock stuff was a little tricky but the software walked me through it.
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