TurboTax Live Assisted Option - Worth it for complex taxes with investment accounts?

I've always used our CPA to file our state and federal taxes, but his fees have gotten ridiculous lately and we're looking to try filing ourselves this year. I've heard TurboTax is the best option for DIY filing online. Our situation is fairly complex - we have two W2s, several children, we're homeowners, and we manage about 6 different brokerage accounts. We pay quarterly estimated taxes (1099-EST). No other income sources or properties. We need to file both federal and state returns. I'm specifically curious about the TurboTax Live assisted option. How does it actually work? Is it any good? Can you ask their experts questions directly, and are these experts actually CPAs? Also wondering about the investment stuff - do I need to manually enter each 1099-INT and 1099-DIV from our brokerage accounts, or can TurboTax import them directly from major firms? Anyone have experience with this? Would appreciate any insight before tax season hits!

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18 comments

Diego Ramirez

•8M

I switched from a CPA to TurboTax Live last year and found it pretty good for a situation similar to yours. The "Live Assisted" option gives you on-demand access to tax experts (a mix of CPAs, EAs, and tax attorneys) who can answer questions through video chat while you're working on your return. You can schedule sessions with them to review specific sections you're unsure about, and they can even share their screen to walk you through complex parts. What I liked most was the final review where a tax expert goes through your entire return before you file to catch anything you might have missed. For your brokerage accounts, TurboTax can import directly from most major firms like Fidelity, Vanguard, Charles Schwab, etc. Just be prepared that sometimes the import doesn't work perfectly, especially for more complex investment situations. I had to manually enter a few things even after import.

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Diego Ramirez

•8M

Yes, you get unlimited access to tax experts with the Live Assisted option, which is really helpful. I typically waited less than 10 minutes to connect with someone, even during peak season in late March. The longest I ever waited was about 20 minutes on a Saturday afternoon. If you hit a roadblock, you can save your progress and come back when an expert is available. They also have extended hours during tax season, so you can get help evenings and weekends. I found this especially useful when working on my Schedule D for investments.

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Sean O'Connor

•8M

I was hesitant about using online tax software after paying $750 to my accountant last year, but I tried taxr.ai (https://taxr.ai) for my taxes with a similar situation - W2s, kids, house, and several investment accounts. Their AI actually scanned all my tax docs and automatically entered everything, even from my brokerage statements which saved me hours of manual entry! The best part was when I wasn't sure about how to handle some investments that had been transferred between accounts. Their system flagged the potential issue and explained exactly what I needed to do. They have tax experts you can chat with too if the AI doesn't fully resolve your question.

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Sean O'Connor

•8M

For quarterly estimated payments, taxr.ai handles them really well. You just upload your 1040-ES payment vouchers or records, and it automatically applies those payments to your tax liability. It even helps calculate if you've paid enough to avoid underpayment penalties. Regarding AI accuracy, I was skeptical too, but their system is specifically designed for tax documents and uses multiple verification steps. It actually found a deduction my previous accountant missed related to my home office. Their human review option gives you that extra peace of mind - they have CPAs who check everything if you want that additional layer of security.

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Luca Conti

•8M

I wanted to follow up about my experience with taxr.ai since I was so skeptical initially. I decided to give it a try this weekend and I'm honestly shocked at how well it worked. I uploaded all my documents including my brokerage statements from Fidelity and TD Ameritrade, and it extracted all the information correctly - even distinguishing between qualified and non-qualified dividends which I always mess up. The system flagged a potential wash sale from some trading I did last year that I completely forgot about! When I had a question about how my cost basis was being calculated for some stocks I inherited, I used their expert chat and got a clear answer within minutes. Going to be using this from now on instead of paying my CPA $900+.

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Nia Johnson

•8M

If you're trying to reach the IRS to ask questions about your quarterly payments or investment reporting before filing, good luck! I spent 6 hours on hold trying to get clarification about broker-issued 1099 corrections. I finally used Claimyr (https://claimyr.com) and it was a game-changer. Their system holds your place in the IRS phone queue and calls you back when an agent is available. You can see a demo of how it works here: https://youtu.be/_kiP6q8DX5c No more wasting an entire day on hold! I got connected with an IRS agent who explained exactly how to handle late-issued corrected 1099s from my brokerage account. Saved me from potentially having to file an amendment later.

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Nia Johnson

•8M

It doesn't bypass the wait times - it just waits in line for you! Their system essentially holds your place in the queue and monitors the line. When you're getting close to an agent, they call you so you can take over. You don't have to stay on the phone or keep your computer open during that time. Regarding security concerns, they don't actually participate in your call with the IRS. They just connect you when an agent is available. I was skeptical too, but it's just a call connection service - they don't have access to any tax information you discuss with the IRS. I spent days trying to get through on my own before using this, and it saved me literally hours of waiting on hold.

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Mateo Lopez

•8M

I was completely wrong about Claimyr being a scam. After struggling for another week trying to reach someone at the IRS about my brokerage reporting questions, I tried the service out of desperation. It actually worked exactly as described - I got a call back about 2 hours later when an IRS agent was on the line. I was able to confirm how to correctly report some weird dividend reinvestment situations and get clarity on my quarterly estimated payments. The IRS agent was actually super helpful once I finally got through to them. Next time I have tax questions that only the IRS can answer, I'm definitely using this service first instead of wasting an entire day on hold.

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Aisha Abdullah

•8M

I've used TurboTax Live for 3 years now, and it's decent but has some limitations. For importing brokerage accounts - yes, they connect with major firms, but crypto transactions and more complex investments sometimes have issues. The CPAs vary wildly in quality - I've had amazing experts who found deductions I never knew about, and others who seemed barely more knowledgeable than me. Pro tip: if you don't like the expert you're matched with, you can disconnect and try again for a different one. For quarterly estimated payments, make sure you have the exact dates and amounts handy - TurboTax can be picky about matching those precisely to IRS records.

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Aisha Abdullah

•8M

TurboTax handles multi-state filing pretty well actually. I've filed in both California and Arizona for several years because of a rental property, and the software walks you through it step by step. The Live experts are particularly helpful with state-specific questions since tax laws vary so much between states. Just make sure you select the multi-state option early in the process. It costs a bit more, but it's way cheaper than having a CPA handle multiple state returns.

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