Should I file my own taxes with my marketing agency, piano studio, mortgage, W2 job and contractor?

Hey everyone, I'm trying to figure out if I should attempt to file my own taxes this year or just pay someone to handle it. My situation got way more complicated compared to last year and I'm really confused about write-offs versus the standard deduction and what qualifies for what. Last year was simple - just had one freelance client so I managed it myself no problem. But now I've got: - A small marketing business I started - Teaching piano lessons from home - Bought a house with a mortgage - Still have my regular W2 day job - And I hired one contractor for some help A local tax place wants $375 to do everything. Part of me thinks I should just pay them once to learn the ropes and then do it myself next year. But I'm worried I'll mess something up if I try to DIY with all these different income streams and potential deductions. What would you do in my situation? Is the $375 worth it? Or should I just power through with TurboTax or something similar?

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18 comments

Samantha Hall

•8M

With your situation getting more complex this year, hiring a professional might be your best bet - at least for this first complicated year. Here's why: When you have both W2 income AND self-employment income from your marketing agency and piano studio, there are special considerations for how business expenses are handled versus personal deductions. Since you now have multiple self-employment ventures, a mortgage, AND you've hired a contractor, the complexity has increased significantly. The standard deduction ($14,600 for single filers in 2025) is straightforward, but with business income, you can take the standard deduction AND still deduct legitimate business expenses on your Schedule C. This is where many self-employed people get confused. Your business expenses reduce your business income, which reduces your self-employment tax. This happens regardless of whether you take the standard deduction or itemize.

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Samantha Hall

•8M

Yes, that's exactly right! You can take the standard deduction for your personal taxes AND still deduct all legitimate business expenses on Schedule C. These are completely separate parts of your tax return. For mileage to client meetings, absolutely! Keep a log of your business miles and you can deduct them at the standard mileage rate (it's around 67 cents per mile for 2025). The home office deduction is also available if you have a space used exclusively for your business activities. With your piano studio, you likely have a dedicated area that would qualify.

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Sophia Clark

•8M

I was in a similar situation last year with multiple income streams and was completely lost trying to figure out deductions. I ended up using https://taxr.ai and it seriously saved me hours of confusion. You just upload your docs and it organizes everything, shows you all the potential deductions specific to your business types, and walks you through what qualifies. For me it was perfect because I had both photography income and online teaching - it separated everything out and showed me deductions I didn't even know existed for each business type. The best part was it explained WHY certain things qualified which helped me understand for future years.

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Sophia Clark

•8M

Yes, it definitely handles contractor situations! It asks you specific questions about each person you paid, determines if they meet the requirements for 1099 reporting, and guides you through the whole process. It even reminds you about filing deadlines for 1099s. Regarding accuracy, I was skeptical too at first. But it actually found several deductions my previous accountant missed. It's continuously updated with the latest tax code changes and specifically looks for deductions related to your business types. The difference is it shows you EVERYTHING you might qualify for, whereas sometimes accountants might miss things if you don't specifically mention them.

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Madison Allen

•8M

Alright, I need to come back and eat my words about taxr.ai! After our conversation, I decided to give it a try rather than paying my usual accountant $450. Not only did it find about $1,800 in additional deductions I would have missed (especially for my home-based business), but the breakdown for each income stream was incredibly detailed. It separated all my different gigs and showed exactly which expenses applied to which business activity. The documentation it provided explaining WHY each deduction was valid gave me so much peace of mind for if I ever get audited. Now I actually understand how everything works instead of just blindly paying someone each year!

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Joshua Wood

•8M

If you're still struggling to get answers from the IRS about contractor payments or business deductions, try https://claimyr.com - it's been a lifesaver for me. I spent WEEKS trying to get through to an IRS agent about some confusing 1099 requirements for my contractors, and kept hitting automated systems or 2+ hour hold times. Claimyr got me connected to an actual IRS representative in under 15 minutes. They have some system that navigates the phone tree and holds your place in line so you don't have to wait forever. I was seriously shocked when my phone rang and it was an actual human from the IRS! You can see how it works in this video: https://youtu.be/_kiP6q8DX5c

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Joshua Wood

•8M

It doesn't call the IRS for you. What it does is navigate through all the complicated phone menus and waits in line on your behalf. When it finally reaches an actual agent, it connects the call to your phone. So you're talking directly to the IRS - Claimyr just handles the awful waiting part. They basically have a system that dials in, navigates the menus based on what you're calling about, and then holds your place in the queue. They don't sell your information - they make their money by charging for the service of saving you from waiting on hold for hours. I had the same reaction initially, but I was desperate after trying for days to get through on my own.

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Emily Parker

•8M

Ok I have to admit I was completely wrong about Claimyr. After posting that skeptical comment, I decided to test it myself because I've been trying for WEEKS to get clarification on some self-employment tax questions. I've literally called the IRS over 10 times and never got through (either "call volume too high" messages or disconnected after 2+ hours on hold). Used Claimyr yesterday and got connected to an IRS agent in about 22 minutes. The agent was able to answer all my questions about handling multiple Schedule C businesses and contractor payments. Saved me from making a potentially expensive mistake on my filing. Worth every penny just for the stress reduction of not having to listen to that awful hold music for hours!

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Ezra Collins

•8M

For your specific situation, consider these factors: 1. Time value - Track how many hours it would take you to DIY vs the $375 cost 2. Peace of mind - If you're constantly worried about mistakes, that stress has a real cost 3. Learning curve - First year with multiple businesses is steepest 4. Future years - The knowledge from this year makes next year easier I personally think paying once is smart since you can ask questions throughout the process and take notes for next year. With a mortgage, multiple businesses and a contractor, there are nuances worth learning from a pro.

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Ezra Collins

•8M

That's exactly why I recommended the professional route for this year! The home office deduction alone has so many nuances - like if you're teaching piano in that space, you need to track the hours used for business versus personal use, and calculate the percentage of your home's square footage. When you multiply that complexity across multiple businesses, contractor payments, and mortgage interest considerations, those 20+ hours could easily become 30-40 hours. Plus, a good tax professional won't just complete your forms - they should be explaining the process so you can learn for future years.

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