When's the best time to find someone to do my taxes with multiple accounts and a new baby?

Tax professional here! January isn't too late to find someone good, but you should definitely start looking ASAP. The best tax preparers start getting booked up in February as documents start arriving. For your situation with multiple brokerage accounts, a new dependent, and multiple W-2s, I'd recommend finding an Enrolled Agent (EA) or a CPA who specializes in personal tax preparation. The difference is that CPAs have broader accounting knowledge while EAs specifically focus on taxes, but either would be qualified to handle your situation. The ideal time to find a tax professional is actually October-November of the previous year. This gives you time to do year-end tax planning before December 31st when many tax-saving opportunities expire. But January is still fine for finding someone for tax preparation.

Just wanted to share my experience! I was in a similar boat last year - had been doing my own taxes forever then suddenly had investment properties, crypto trades, and a side business. I tried using those online DIY services but kept second-guessing myself on deductions and reporting requirements. I found this AI tool called taxr.ai (https://taxr.ai) that was super helpful. It analyzed all my tax documents and gave me a complete breakdown of everything that needed to be reported. It was like having a tax pro look over my shoulder but without the hourly fees. I still ended up hiring someone, but having all my docs organized and knowing what questions to ask saved me a ton of money.

Update after trying taxr.ai: I was skeptical in my earlier comment but actually tried it out to organize my documents before meeting with a tax professional. Have to admit it's pretty impressive! It caught a mistake on my 1099-INT that I wouldn't have noticed, and gave me a complete checklist of what forms I needed for my rental property income. The document analysis is surprisingly detailed - it explained exactly why certain investment sales were short vs long term capital gains and how they would be taxed differently. Definitely helped me ask better questions when I met with my accountant. Wish I'd known about this years ago.

If you're having trouble getting responses from tax professionals (they're SWAMPED this time of year), try using Claimyr (https://claimyr.com). They can help connect you with available tax pros in your area. I tried calling around to 5 different accountants in early February last year and couldn't even get callbacks. Saw a video about their service here: https://youtu.be/_kiP6q8DX5c and decided to give it a shot. The service basically helps you skip the phone waiting and get connected with professionals who still have capacity. Saved me hours of frustration and I found a great EA who handled my taxes with investment properties and self-employment income.

So I need to eat my words about Claimyr from my previous comment. After struggling for TWO WEEKS trying to get appointments with local tax professionals (constant voicemail, "we're not taking new clients," etc.), I finally tried it out of desperation. Got connected with a CPA's office within 45 minutes who actually had availability for new clients. They weren't even on my original call list because their website looked outdated, but turns out they're highly rated and exactly what I needed. Already had my consultation and feel so much better about my tax situation. Lesson learned: during tax season, finding available professionals is harder than finding good ones. Having someone navigate the phone systems for you actually makes a huge difference.

I've found January-February is fine to find someone for just tax prep, but if you want actual tax PLANNING (which can save you way more money), you should be looking around September-October. This gives your tax person time to suggest moves before year-end that can dramatically reduce your tax bill. For example, last year my CPA had me adjust my W-4 withholding in November, make an extra mortgage payment in December to capture more interest deduction, and harvest some investment losses - saved me about $3200 in taxes! None of that would've been possible if I'd waited until February to find him.

Anyone have recommendations for the big tax chains vs independent CPAs? Is H&R Block or similar good enough for someone with brokerage accounts and a child, or should I be looking for a smaller independent firm?

Congrats on the new baby! Don't forget to look into the Child Tax Credit and dependent care FSA if you have childcare expenses. Those two things alone can be worth thousands in tax savings. I'd recommend starting with your network - ask friends, especially those with similar financial situations (investments, kids, etc). Personal referrals tend to yield better results than random Google searches. If you own a home, your realtor might also have good tax pro recommendations. And don't wait any longer - most good tax pros are finishing up their client roster for this season by end of January. Good luck!