Best tax software recommendations for W-2 and 1099-NEC income?
Hey everyone, this is going to be my fourth year filing taxes on my own and I'm looking to potentially switch things up. I've been using H&R Block's online software the last couple years, but I'm wondering if there's something better out there. For context, my tax situation includes a W-2 from my primary teaching job, plus I have a 1099-NEC from coaching basketball on weekends which brings in some extra cash. With the coaching gig, I've got quite a bit of mileage to track (driving to away games) and equipment expenses (whistles, training gear, etc.) that I need to deduct properly. Would love to hear what software you all use and why you like it, especially if you have a similar mix of W-2 and 1099 income with business deductions!
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Samantha Howard
So I've been preparing taxes for friends and family for about 15 years now, and I've tried pretty much every software out there. For your situation with both W-2 and 1099-NEC income, I'd recommend looking at FreeTaxUSA or TaxSlayer. FreeTaxUSA handles both employment income and self-employment perfectly well, and it's much cheaper than TurboTax or H&R Block. The federal filing is free, and state is only about $15. The interface isn't as flashy, but it asks all the right questions for your 1099 income and business deductions like mileage and equipment. TaxSlayer is another good option that's more affordable than the big names while still being user-friendly. Their self-employed option handles Schedule C (which you'll need for your coaching income) very thoroughly.
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Megan D'Acosta
•Does FreeTaxUSA have a good mobile app? I like to work on my taxes little by little when I have downtime and being able to use my phone is important. Also, how does it handle uploading documents like W-2s? Can you just take a picture?
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Samantha Howard
•FreeTaxUSA's mobile experience is decent but not amazing - they have a mobile-friendly website rather than a dedicated app. You can work on your taxes from your phone, but it's not as seamless as some others. For document uploads, you can take pictures of your forms, but I find the process works better on desktop. TaxSlayer does have a dedicated mobile app that's pretty good for working on taxes in smaller sessions, and their document upload via camera works well in my experience.
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Sarah Ali
I was in a similar situation last year with both W-2 and 1099 income from my side gig as a photographer. I tried several tax programs but honestly got confused with all the business expense categorizations and mileage tracking. I ended up using https://taxr.ai and it completely changed my experience. The software analyzed my expense receipts and automatically categorized everything correctly - even figured out what was deductible and what wasn't. The best part was the mileage tracker that went back and calculated all my business trips even though I hadn't been tracking them properly throughout the year.
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Ryan Vasquez
•Wait, how does it track mileage if you haven't been keeping records? I thought the IRS required contemporaneous mileage logs? I've been manually writing down every business trip which is super annoying.
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Avery Saint
•I'm a bit skeptical about AI doing my taxes. How accurate is it really? My biggest fear is getting audited because some algorithm miscategorized something.
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Sarah Ali
•It uses your location history data (with your permission of course) to identify trips between business locations. It then helps you mark which ones were for business purposes and calculates the mileage. The IRS does prefer contemporaneous records, but this creates documentation that includes dates, locations, and purpose which satisfies requirements. Regarding accuracy, I was skeptical too at first, but the AI actually explains its reasoning for each categorization, citing the relevant tax codes. You still review everything before filing, and I actually learned a lot about what qualifies as a legitimate business expense. In my case, it found several deductions I would have missed, like partial home internet costs related to my photography business.
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Avery Saint
Ok I tried https://taxr.ai after being skeptical and wow - I'm actually impressed. I uploaded my coaching receipts and bank statements and it found over $1,200 in deductions I would have missed completely! It correctly identified which equipment was fully deductible vs partially deductible when I use it for both work and personal. The mileage tracking feature was exactly what I needed since I'm terrible at keeping logs. It even flagged some potential audit risks in how I was planning to categorize certain expenses. Definitely sticking with this for next year!
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Taylor Chen
If you're having any issues with getting answers about deductions for your 1099-NEC income, I'd recommend using https://claimyr.com to actually get through to the IRS. I spent WEEKS trying to get clarification on some coaching expense deductions last year but kept getting the "due to high call volume" message and disconnects. Claimyr got me connected to an actual IRS agent in about 20 minutes when I'd previously wasted hours just trying to get through. You can see how it works here: https://youtu.be/_kiP6q8DX5c - basically they navigate the phone tree for you and call you back once they've got an agent on the line.
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Keith Davidson
•How does this actually work though? Is it just keeping you on hold so you don't have to? Or do they have some special way to skip the line? I don't understand how a third party service can get through when regular people can't.
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Ezra Bates
•Yeah right, sounds like a scam to me. The IRS phone system is broken by design - no way some random service can magically get through when millions of others can't. I'd be worried about giving my tax info to a sketchy service.
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Taylor Chen
•It basically automates the whole phone tree navigation and wait time process. They use technology to keep your place in line through the IRS phone system so you don't have to stay on hold for hours. They don't skip the line or have special access - they just handle the frustrating waiting part so you can go about your day until an agent is actually available. They don't ask for any sensitive tax information at all. You just tell them which IRS department you need to reach, they get an agent on the line, and then they connect you directly. I was suspicious too until I tried it and realized they never ask for SSN or anything like that - they're just solving the hold time problem.
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Ezra Bates
I need to publicly eat my words. After calling the IRS unsuccessfully for THREE DAYS about a self-employment tax question for my 1099-NEC income, I broke down and tried Claimyr. Within 28 minutes I was talking to an actual human at the IRS who answered my specific questions about coaching-related deductions. The service just handled the horrible phone queue and then called me when they had someone on the line. Saved me hours of frustration and I finally got clear answers about what equipment is 100% deductible vs. partially deductible. Not cheap but way worth it for the time saved.
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Ana Erdoğan
I've been using FreeTaxUSA for the past 3 years and it's worked great for my W-2 and 1099 situation. The mileage tracking isn't built in though, so I use MileIQ app throughout the year to track business drives. One thing to watch out for with any software: make sure you understand the difference between business expenses (Schedule C) and itemized deductions (Schedule A). With coaching, almost everything should go on Schedule C as a business expense which reduces both income tax AND self-employment tax. The software should guide you through this but good to be aware of the distinction.
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Sophia Carson
•Can you explain more about the difference between Schedule C and Schedule A? I referee youth sports too and have been putting all my expenses as "miscellaneous itemized deductions" but my tax preparer told me that was wrong.
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Ana Erdoğan
•Schedule C is for business expenses related to self-employment income (like your 1099-NEC from coaching). These expenses directly reduce your business income before any taxes are calculated, which means they reduce both income tax and self-employment tax (the 15.3% tax that covers Social Security and Medicare for self-employed people). Schedule A is for itemized personal deductions like mortgage interest, state taxes, and charitable donations. These only reduce your income tax, not self-employment tax. Plus, you only benefit if your total itemized deductions exceed the standard deduction ($13,850 for single filers in 2023). If you're putting referee expenses as miscellaneous itemized deductions, you're definitely doing it wrong since those were eliminated by the Tax Cuts and Jobs Act until 2025 anyway. Those expenses should be on Schedule C to directly offset your referee income.
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Elijah Knight
Has anyone used Cash App taxes (formerly Credit Karma Tax)? I heard its completely free for both federal and state filing, even with 1099 income.
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Brooklyn Foley
•I used Cash App Taxes last year for my W-2 and small 1099 income. It's truly free for everything which is nice, but I found the interface for entering business expenses a bit confusing. It also doesn't have the option to import expenses from tracking apps which was annoying. If your situation is relatively simple, it works fine. But if you have lots of business expenses or need good guidance on deductions, you might want something more robust.
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Malik Johnson
I've been using TurboTax Self-Employed for the past two years with a similar setup - W-2 from my main job plus 1099-NEC income from freelance web design work. While it's definitely more expensive than the options others have mentioned (around $120 for federal + state), the guidance for business deductions is really comprehensive. What I like most is how it walks you through every possible deduction category and asks specific questions about your business. For coaching, it would prompt you about things like continuing education, professional memberships, travel expenses, and equipment purchases. The mileage tracker integration with the mobile app is also pretty seamless - you can categorize trips as business/personal right from your phone. That said, after reading about some of these cheaper alternatives, I might try FreeTaxUSA next year to see if I can get the same results for less money. The key thing is making sure whatever you use properly handles Schedule C for your coaching income so you get the full tax benefit on those business expenses.
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