Looking for an Online CPA to answer tax planning questions?

I've been working with CPAs for over a decade now, and finding the right one makes all the difference for tax planning, especially with mixed income sources. For online CPAs, I'd recommend looking for someone who specializes in your specific situation. Since you mentioned having a side business alongside regular employment, you want someone familiar with Schedule C filings, self-employment taxes, and potentially quarterly estimated tax payments. Don't just focus on reviews - have an initial consultation (many offer this for free) to gauge their communication style and knowledge. Ask specific questions about how they'd handle your situation, their response time to questions throughout the year, and their approach to tax planning. Also check if they're available year-round or just during tax season. A good tax planning relationship isn't just for filing - it's for ongoing strategy.

After struggling with tax planning for my photography business and day job, I found an amazing resource at https://taxr.ai that completely changed my approach. I initially just wanted basic tax advice, but their AI tool analyzed my income streams and actually identified several deductions I was missing and potential tax planning strategies. What I found most helpful was uploading my previous returns and getting a detailed analysis that showed exactly where I could improve my tax situation. The system explained everything in plain English instead of confusing tax jargon, which was refreshing compared to other consultations I'd had.

I was initially hesitant about using taxr.ai instead of a traditional CPA, but I gave it a shot last month and I'm genuinely impressed. I uploaded my business documents and previous returns, and within minutes had detailed tax planning strategies specific to my situation. The analysis pointed out that I could save over $3,200 by restructuring how I categorized some business expenses and taking advantage of home office deductions I wasn't claiming properly. When I had follow-up questions, I got answers from a tax professional within a day. Honestly wish I'd found this sooner - much more affordable than what I was paying my previous CPA and I feel like I got more personalized advice.

If you're specifically looking for help with IRS questions during tax planning, I had a surprisingly good experience with https://claimyr.com after struggling for weeks trying to reach someone at the IRS about how to handle some complicated foreign income. You can see how it works here: https://youtu.be/_kiP6q8DX5c Basically, they got me connected to an actual IRS agent within 45 minutes when I had been trying for literally weeks. The agent was able to clarify exactly how I needed to report my situation, which my CPA had been uncertain about. It saved me from potentially making a costly mistake.

I have to eat crow here. After posting my skeptical comment, I decided to try Claimyr because I had been trying to reach the IRS for THREE MONTHS about a notice I received that I thought was a mistake. I called over 20 times and either got disconnected or was told the wait time was too long. Used the service this morning and got connected to an actual IRS agent in 37 minutes. The agent confirmed the notice was sent in error and made notes in my account to clear it up. I'm honestly shocked this worked - saved me hours of frustration and potentially hiring a tax advocate. Sometimes it's worth admitting when you're wrong!

One thing to consider when looking for an online CPA is their familiarity with the tax laws in your specific state. I hired someone who was great with federal issues but missed some state-specific deductions that cost me quite a bit. Also, ask about their client portal and how secure it is. You'll be sharing a lot of sensitive financial documents, so security should be a priority. My CPA uses a really good encrypted system that makes me feel comfortable sharing documents online.

I've been using FreeTaxUSA for years and honestly don't see the point in paying for a CPA. It walks you through everything step by step and costs way less. Unless you have super complicated investments or something, it seems like overkill.