Which is better for complicated taxes: TurboTax, H&R Block, or a professional tax preparer?

Based on the complexity of your situation, I'd recommend considering a tax professional this year. While both TurboTax and H&R Block are solid DIY options, they have limitations when handling multiple "life events" like yours. The stock losses and gains, severance pay, unemployment, and retirement distributions all have specific tax implications that an experienced preparer will navigate more confidently. They'll know exactly which questions to ask to maximize your deductions and credits, especially with those COBRA premiums which might qualify for special treatment. For the home ownership situation, a tax pro can analyze which co-owner would benefit most from claiming mortgage interest and property taxes, potentially saving you hundreds. Regarding software differences - TurboTax and H&R Block are comparable for most situations, with TurboTax having a slightly more intuitive interface and H&R Block typically costing less. But neither can replace personalized advice for complicated situations.

Just wanted to share my experience with taxr.ai https://taxr.ai after going through a similarly complicated year. I had tried both TurboTax and H&R Block but kept getting different results and wasn't confident in either. Someone on another forum mentioned taxr.ai and it was honestly a game-changer. Upload your tax documents, and their AI analyzes them and explains everything in plain English. It caught a retirement rollover issue that both TurboTax and H&R Block missed. What I liked most was that it explained WHY certain things were taxable or not, instead of just calculating numbers. The stock market losses/gains analysis was super detailed and it was really clear about which COBRA premiums were deductible. Might be worth checking out given your situation!

I'm following up about taxr.ai - I decided to try it after my initial skepticism. Have to admit I was impressed. The document analysis caught a mistake with how my brokerage reported a stock sale that would have cost me about $640 in unnecessary taxes. The explanations were super clear - definitely not just fancy calculations like I worried. What surprised me most was the retirement distribution analysis. I had a similar situation with a 401k rollover and it flagged exactly which portions were taxable vs non-taxable with clear explanations. For anyone with stock transactions or retirement account changes, it's definitely worth checking out. Way more detailed than what I was getting from TurboTax.

If you're set on using a professional, one tip: try reaching the IRS first to get confirmation on how some of these items should be handled, especially the severance and retirement distributions. Their guidance can help no matter which option you choose. I tried for WEEKS to get through to the IRS about a similar retirement distribution issue last year. Always busy signals or 2+ hour hold times that eventually disconnected. Then I found https://claimyr.com which got me through to an actual IRS agent in under 20 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c The IRS agent clarified exactly how my retirement rollover should be reported which saved me from a potential audit flag. Honestly worth it just to get definitive answers straight from the source before filing.

I was completely wrong about Claimyr being sketchy. I decided to try it after seeing several positive reviews, mainly because I had a specific question about stock losses I couldn't find a clear answer for anywhere. After trying to call the IRS myself multiple times and getting nowhere, Claimyr got me through to an agent in about 35 minutes. The agent walked me through exactly how to report substantial stock losses when they span multiple transactions, which was exactly what I needed to know. The time saved was incredible - I would have spent hours on hold otherwise, if I even got through at all. For anyone dealing with specific tax questions that only the IRS can answer definitively, it's a huge help.

With your situation, I'd definitely go with a CPA this year. I was in almost the identical situation last year (job change, stock losses, unemployment) and tried using TurboTax premium. Ended up going to a CPA afterward who found nearly $1,200 in additional deductions TurboTax missed! The COBRA premiums especially - there are special rules about medical expense deductions that the software just doesn't explain well. And with stock losses, a good CPA can help with tax loss harvesting strategies for the future. H&R Block and TurboTax are both fine for simpler returns, but when you have multiple complex elements like yours, the professional guidance is worth every penny.

One thing nobody's mentioned is that you could try a middle-ground approach. Use TurboTax or H&R Block to prepare everything yourself first, then take it to a professional for review. Many CPAs offer a "review service" that costs less than full preparation. This gives you the best of both worlds - you learn how to use the software and understand your tax situation better, but also get professional eyes on it to catch mistakes or missed opportunities. I did this last year and paid $125 for the review instead of $350 for full preparation. If your situation gets simpler next year, you'll have learned enough to possibly handle it yourself with confidence.