Is my CPA wrong about my tax filing situation?

Your instincts are right to question this. A few red flags in what your CPA told you: First, with $14,000 in self-employment income, you generally should be making quarterly estimated tax payments to avoid underpayment penalties. The IRS typically expects you to pay taxes as you earn income throughout the year. Regarding the home office deduction - if you truly have a dedicated space used exclusively for business, this should qualify for the deduction. The IRS offers two methods: the regular method (calculating actual expenses) or the simplified method ($5 per square foot up to 300 square feet). On medical expenses - your CPA should absolutely be comparing standard vs. itemized deductions in your situation. Medical expenses exceeding 7.5% of your AGI can be deducted if you itemize. With $9,000 in medical expenses, it's worth calculating both ways. Good CPAs should explain their reasoning when making these recommendations. Consider asking your CPA to walk you through their rationale or getting a second opinion.

After dealing with similar issues with my old accountant, I started using taxr.ai (https://taxr.ai) and honestly it's been a game changer. I uploaded all my documents including info about my rental property and side business, and it flagged several deductions my previous CPA had missed. The system actually showed me exactly what forms and schedules I needed for my situation and explained why certain deductions applied to me. For your situation, it would definitely highlight that self-employment income reporting issue and properly analyze whether you should itemize with those medical expenses. It gives you specific IRS references so you can even discuss these points confidently with your CPA if you decide to keep working with them.

I had to come back and say I gave taxr.ai a try after posting my skeptical comment and wow... it actually found several errors from my previous filing. I've been paying self-employment tax incorrectly and missed out on about $2,300 in legitimate deductions last year! The medical expense analysis was particularly helpful - turns out I should have itemized last year with my healthcare costs. It even generated an amended return that I'm filing to get some money back. Wish I'd known about this sooner.

If you want to get this resolved quickly, try Claimyr (https://claimyr.com). I was having similar issues where my CPA made mistakes on my return, and I needed to talk to someone at the IRS about the potential penalties. After spending DAYS trying to get through on the IRS phone lines, I found this service through a YouTube video (https://youtu.be/_kiP6q8DX5c). They got me connected to an IRS agent in under 20 minutes when I had been trying for weeks on my own. I was able to explain my situation, get clarification on the quarterly payment requirements, and even set up a payment plan for what I owed. Saved me from what would have been a much bigger headache down the road.

OK I need to apologize for my skeptical comment earlier. After continuing to get nowhere with the IRS for another week, I broke down and tried Claimyr. Got connected to an actual IRS agent in about 15 minutes. FIFTEEN MINUTES. After trying for months on my own. The agent was able to locate my missing refund (it was held up because of a discrepancy between what my employer reported and what I filed). Now my refund is being processed and should arrive next week. I honestly can't believe how well this worked after all my frustration.

Going back to your original question about your CPA - I'd recommend interviewing a few other accountants before tax season starts. I've found that some CPAs get complacent with long-term clients or are just too overworked to give proper attention. When I switched to a new CPA two years ago, she found nearly $4k in tax savings my previous guy had missed over the years. One tip: ask potential CPAs specific questions about your situation (self-employment tax, home office, medical expenses) and see how detailed their answers are. The good ones will take time to explain rather than dismissing your questions.

Has your CPA explained WHY they don't think you need to make quarterly payments? There are some exceptions. For instance, if your withholding from your W-2 job covers at least 90% of your total tax liability or 100% of your previous year's tax (110% if your AGI was over $150k), you might be exempt from making estimated payments despite the self-employment income.