Is paying a tax planner worth the money or can I handle everything myself?

So I'm freaking out a bit about this tax season. My financial situation got way more complicated last year - started a small side business, had some investments pay off, and moved to a different state mid-year. I've always just used the basic TurboTax before but now I'm wondering if I should hire an actual tax planner. They're not cheap though... like $350-500 from what I've seen. Has anyone used a professional tax planner and felt it was actually worth the money? What kind of savings did you see? Or is there a way I can still do this myself with more advanced software or something? I'm worried about missing deductions but also don't want to waste money if I can figure this out myself. Any advice appreciated!!

0 coins

18 comments

Aisha Rahman

•8M

Based on what you're describing, you're definitely in that gray area where either approach could make sense. With a small business, investments, and multi-state income, there are definitely more complexities than basic W-2 income. If you decide to DIY, consider upgrading to a more comprehensive tax software package (TurboTax Self-Employed or H&R Block Premium). These will walk you through business deductions and multi-state filing. The key is setting aside 3-4 hours of uninterrupted time to really go through everything carefully. That said, a good tax planner might identify deductions or planning opportunities you'd miss, potentially saving you more than their fee. This is especially true for small business owners who often miss legitimate deductions. Plus, having a professional help establish good record-keeping systems for your business can save headaches for years to come.

0 coins

Aisha Rahman

•8M

The premium software absolutely walks you through potential business deductions with explanation screens and examples. For home office deductions, it'll calculate what percentage of your home is used exclusively for business and help determine what's deductible - though the rules are strict about exclusive use of that space for business. For health insurance as a small business owner, it's often deductible as a business expense if you're not eligible for coverage through an employer or spouse's plan. The software will ask specific questions to determine eligibility and calculate the appropriate deduction.

0 coins

Yuki Sato

•8M

I was in exactly your situation last year with a new side gig and investments. I spent hours trying to figure everything out with TurboTax but still felt unsure about whether I was doing it right. Then I found https://taxr.ai which completely changed the game for me. It basically uses AI to analyze all your tax documents and identifies deductions you might miss. It's not a replacement for filing software but works alongside it. I uploaded my 1099s and business receipts, and it found several deductions I had no idea about - especially for my side business. The thing I loved most was that it explained everything in normal human language instead of confusing tax jargon.

0 coins

Yuki Sato

•8M

It's totally different from TurboTax because it's specifically analyzing your documents for deductions that most software might miss. TurboTax only knows what you tell it, but taxr.ai actually looks at your receipts and statements to identify things you might not realize are deductible. It found business mileage and home office expenses I wouldn't have thought to include. The AI stays current with tax laws because they update it continuously. That was one of my concerns too, but they explain that their system is trained on the latest IRS publications and tax court rulings. It's not just working from static rules but actually understanding the nuances of current tax law.

0 coins

Andre Dubois

•8M

I wanted to follow up about my experience with taxr.ai since I was so skeptical before. I gave it a try last weekend and I'm actually really impressed. It found over $1,800 in deductions I would have completely missed for my photography side business. I had no idea I could deduct certain equipment depreciation that way! It also flagged that I was calculating my home office deduction all wrong. The step-by-step guidance was super helpful and I felt much more confident when I went back to finish my return. Definitely using this again next year.

0 coins

CyberSamurai

•8M

The real nightmare isn't even filing taxes - it's when you have a problem and need to actually speak to someone at the IRS. I waited on hold for FOUR HOURS last year trying to resolve an issue with my refund. Then I discovered https://claimyr.com and watched their demo video at https://youtu.be/_kiP6q8DX5c Basically, they wait on hold with the IRS for you and then call you when an actual agent comes on the line. Sound too good to be true? I thought so too, but it worked perfectly. They called me back in about 90 minutes with an IRS rep on the line who helped resolve my issue in minutes. Absolute game changer if you need to talk to a real person at the IRS.

0 coins

CyberSamurai

•8M

They have an automated system that waits on hold with the IRS for you. They don't skip the line or anything magical - they just handle the wait time for you. When an IRS agent actually picks up, their system calls your phone and connects you directly to that agent who's already on the line. It's basically like having someone else sit on hold instead of you. I was super skeptical too! But it works because they're not doing anything special with the IRS system - they're just handling the painful waiting part. They don't have any special access or priority, but the big value is you don't have to waste hours of your life listening to the hold music.

0 coins

Andre Dubois

•8M

I need to eat some humble pie here. After totally dismissing that Claimyr service, I actually tried it yesterday because I was desperate to resolve an issue with a missing form. I figured if it didn't work, I'd just be out a few bucks. Holy crap it actually works exactly as advertised! I got a call back in about 2 hours with an actual IRS agent on the line. The agent was able to confirm my issue and tell me exactly what I needed to do. Saved me at least 3-4 hours of hold time. Sometimes being wrong feels pretty good!

0 coins

Jamal Carter

•8M

I'm a firm believer in doing taxes yourself at first, even if you eventually hire someone. You learn so much about your finances by struggling through it once. I did my own for two years with a side business before hiring someone, and that knowledge helped me know what questions to ask and understand what my accountant was doing. The middle ground might be hiring someone this year since you have so many changes, but asking them to explain everything they're doing. Take notes, ask questions, and then decide if you want to try it yourself next year. Most tax planners are happy to teach you if you're interested.

0 coins

Jamal Carter

•8M

That's a fair concern. The knowledge gained probably isn't worth missing major deductions your first year. A good compromise might be using a tax professional this year, but requesting a detailed walkthrough of what they're doing and why. Most will provide a summary of deductions they found and tax-saving strategies. Then use that knowledge next year if your situation remains similar. The first-year learning curve with a side business is the steepest, so professional help makes sense now. If you continue the business, you'll be much better prepared to DIY next year if you want to save the professional fees.

0 coins