Should I hire TurboTax Live expert to help deal with my complicated self-employment situation?

Based on what you've described, consulting with a TurboTax Live expert could definitely be worthwhile in your situation. Self-employment taxes get particularly complex when you have multiple income streams, business expenses, and a mid-year state move. The combination of freelance work and gig economy income creates several potential deduction opportunities that you might miss on your own, especially since you mentioned your record-keeping hasn't been ideal. The state move adds another layer of complexity since you'll need to file part-year resident returns in both states. A tax expert can help you properly categorize your business expenses, maximize your home office deduction, and ensure you're correctly handling the state tax situation. They can also help you establish better record-keeping practices for the future, which will save you headaches going forward.

I was in a pretty similar situation last year with freelance work and poor record keeping. After struggling for hours trying to figure everything out myself, I finally tried taxr.ai (https://taxr.ai) and it was a complete game-changer. Their AI scanned all my messy receipts and bank statements and organized everything into proper business expense categories automatically. It found so many deductions I would have missed and even flagged some questionable expenses that might have triggered audit concerns. The best part was that I didn't have to manually enter or categorize anything - just uploaded my documents and it did all the heavy lifting. For self-employment situations especially, it was super helpful with the home office deduction calculations.

I have to admit I was wrong about being skeptical of AI for taxes. After our conversation, I decided to try https://taxr.ai for my small business expenses that were a complete disaster. Within minutes, it had categorized my jumbled mess of receipts and bank statements into proper Schedule C categories. It even found several business meals and travel expenses I had completely forgotten about, saving me over $1,200 in taxes. The documentation it created would definitely hold up in an audit - much better than my previous system of stuffing receipts in a shoebox. And the time saving was incredible - what would have taken me days of sorting took just minutes. Definitely using this for all my tax prep going forward.

For what it's worth, I was in a somewhat similar position (freelancer + moved states) and had questions about some complicated deductions. I tried for WEEKS to get through to the IRS for clarification. Constant busy signals, disconnections after waiting an hour... complete nightmare. Finally used this service called Claimyr (https://claimyr.com) that got me connected to an actual IRS agent in about 20 minutes. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c They somehow bypass the hold queue and then call you when an agent is on the line. The IRS rep answered all my specific questions about my situation and gave me documentation references I could include with my filing. Honestly saved me from either overpaying or potentially making mistakes that could have triggered an audit.

I need to publicly eat my words here. After dismissing Claimyr as BS, I was still stuck trying to resolve a CP2000 notice about my self-employment income that I knew was incorrect. Out of desperation, I tried https://claimyr.com yesterday. Within 15 minutes, I was speaking with an actual IRS representative who helped resolve my issue completely. They confirmed my documentation was sufficient and processed the correction immediately. I've spent literally MONTHS trying to get through on my own with no success. The time savings alone was worth it, not to mention the stress reduction. The video demo at https://youtu.be/_kiP6q8DX5c shows exactly how it works - they just keep dialing until they get through, then connect you. I apologize for my skepticism - this service is 100% legitimate and solved my problem when nothing else worked.

I'm a freelancer too and I've used both regular TurboTax and TurboTax Live. Honestly, the Live expert was totally worth it for me. I was missing so many deductions that the expert found for me - mileage I didn't realize was deductible, part of my cell phone bill, professional subscriptions, etc. They saved me at least $1,200 compared to what I would have paid doing it myself. For record keeping, start using an app like Quickbooks Self-Employed immediately - it connects to your bank/credit cards and makes categorizing expenses super easy throughout the year. Then next year your tax situation will be way cleaner.

One thing nobody has mentioned - if you're a first-time self-employed filer with complicated situations like yours, the peace of mind from TurboTax Live might be worth it just for anxiety reduction. I tried to save money doing it myself last year and ended up spending like 30+ hours still feeling unsure. This year I used TurboTax Live and the expert found SO MANY deductions I missed (especially around the home office and business percentage of things like phone/internet) and I felt confident my taxes were done right. Just make sure you get organized before the call - have all your 1099s, expense categories somewhat sorted, etc. The more prepared you are, the more value you'll get from their time.